CA1077945A - Method for the direct manufacture of n-acyl derivatives of alpha-amino-gamma-keto acids and compounds thereof - Google Patents

Method for the direct manufacture of n-acyl derivatives of alpha-amino-gamma-keto acids and compounds thereof

Info

Publication number: CA1077945A
Authority: CA; Canada
Prior art keywords: alpha; acid; beta; gamma; adduct
Prior art date: 1975-09-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA259,378A

Other languages

English (en)

French (fr)

Inventor

Dov Ben-Ishai

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Technion Research and Development Foundation Ltd

Original Assignee

Technion Research and Development Foundation Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-09-04

Filing date

1976-08-18

Publication date

1980-05-20

1976-08-18 Application filed by Technion Research and Development Foundation Ltd filed Critical Technion Research and Development Foundation Ltd

1980-05-20 Application granted granted Critical

1980-05-20 Publication of CA1077945A publication Critical patent/CA1077945A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 34
238000004519 manufacturing process Methods 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 title abstract description 20
238000006243 chemical reaction Methods 0.000 claims abstract description 23
238000002360 preparation method Methods 0.000 claims abstract description 18
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims abstract description 17
150000002148 esters Chemical class 0.000 claims abstract description 9
150000003140 primary amides Chemical class 0.000 claims abstract description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
239000003377 acid catalyst Substances 0.000 claims abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 28
-1 aryloxy radical Chemical group 0.000 claims description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
JOOXCMJARBKPKM-UHFFFAOYSA-N laevulinic acid Natural products CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 18
229940040102 levulinic acid Drugs 0.000 claims description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
GCWCVCCEIQXUQU-UHFFFAOYSA-N alpha-hydroxyhippuric acid Chemical compound OC(=O)C(O)NC(=O)C1=CC=CC=C1 GCWCVCCEIQXUQU-UHFFFAOYSA-N 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
ONJSZLXSECQROL-UHFFFAOYSA-N alpha-hydroxyhippuric acid Natural products OC(=O)CNC(=O)C1=CC=CC=C1O ONJSZLXSECQROL-UHFFFAOYSA-N 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
150000002596 lactones Chemical class 0.000 claims description 7
CIMBHEAROUDHSI-UHFFFAOYSA-N 2-benzamido-4-oxopentanoic acid Chemical compound CC(=O)CC(C(O)=O)NC(=O)C1=CC=CC=C1 CIMBHEAROUDHSI-UHFFFAOYSA-N 0.000 claims description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
150000005840 aryl radicals Chemical class 0.000 claims description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 claims description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
JQEZLSUFDXSIEK-UHFFFAOYSA-N 2-hydroxy-2-(phenylmethoxycarbonylamino)acetic acid Chemical compound OC(=O)C(O)NC(=O)OCC1=CC=CC=C1 JQEZLSUFDXSIEK-UHFFFAOYSA-N 0.000 claims description 3
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 3
239000004471 Glycine Substances 0.000 claims description 3
NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 3
FNENWZWNOPCZGK-UHFFFAOYSA-N ethyl 2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(C)=O FNENWZWNOPCZGK-UHFFFAOYSA-N 0.000 claims description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
235000011007 phosphoric acid Nutrition 0.000 claims description 3
229910015900 BF3 Inorganic materials 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims 8
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
229960004838 phosphoric acid Drugs 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 3
125000005594 diketone group Chemical group 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 2
125000004989 dicarbonyl group Chemical group 0.000 abstract 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
230000008018 melting Effects 0.000 description 11
238000002844 melting Methods 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 7
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229940032330 sulfuric acid Drugs 0.000 description 4
SQEBMLCQNJOCBG-HVHJFMEUSA-N (5s)-3-(hydroxymethyl)-5-methoxy-4-methyl-5-[(e)-2-phenylethenyl]furan-2-one Chemical compound C=1C=CC=CC=1/C=C/[C@]1(OC)OC(=O)C(CO)=C1C SQEBMLCQNJOCBG-HVHJFMEUSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
FBMORZZOJSDNRQ-UHFFFAOYSA-N Demethoxy,B,HCl-Adriamycin Natural products C1C2C(=C)CCCC2(C)CC2(O)C1=C(C)C(=O)O2 FBMORZZOJSDNRQ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
229930188620 butyrolactone Natural products 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
JUTMAMXOAOYKHT-UHFFFAOYSA-N karrikinolide Natural products C1=COC=C2OC(=O)C(C)=C21 JUTMAMXOAOYKHT-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000002994 raw material Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
230000009466 transformation Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
JAOACKUHEYGJCB-UHFFFAOYSA-N 2-benzamido-4-oxo-4-phenylbutanoic acid Chemical compound C(C1=CC=CC=C1)(=O)NC(C(=O)O)CC(C1=CC=CC=C1)=O JAOACKUHEYGJCB-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 2
238000005830 amidoalkylation reaction Methods 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
238000001665 trituration Methods 0.000 description 2
YXEMSDUZZWSYFL-UHFFFAOYSA-N 3-acetyl-2-benzamido-4-oxopentanoic acid Chemical compound CC(=O)C(C(C)=O)C(C(O)=O)NC(=O)C1=CC=CC=C1 YXEMSDUZZWSYFL-UHFFFAOYSA-N 0.000 description 1
AUZFRUHVDNDVJI-UHFFFAOYSA-N 3-acetylpentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)C(C)=O AUZFRUHVDNDVJI-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical compound OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 description 1
YNKQMZRTPPVLLL-UHFFFAOYSA-N 5,5-Dimethyl-2(5H)-furanone Chemical compound CC1(C)OC(=O)C=C1 YNKQMZRTPPVLLL-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001371 alpha-amino acids Chemical class 0.000 description 1
235000008206 alpha-amino acids Nutrition 0.000 description 1
150000001408 amides Chemical group 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 1
HJCMMOODWZOXML-UHFFFAOYSA-N bromo hypobromite Chemical class BrOBr HJCMMOODWZOXML-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004721 gamma keto acids Chemical class 0.000 description 1
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
DTJIUHHLSRUUKI-UHFFFAOYSA-N methyl 2-benzamido-4-oxopentanoate Chemical compound COC(=O)C(CC(C)=O)NC(=O)C1=CC=CC=C1 DTJIUHHLSRUUKI-UHFFFAOYSA-N 0.000 description 1
150000004682 monohydrates Chemical group 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000000844 transformation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA259,378A 1975-09-04 1976-08-18 Method for the direct manufacture of n-acyl derivatives of alpha-amino-gamma-keto acids and compounds thereof Expired CA1077945A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IL48047A IL48047A0 (en)	1975-09-04	1975-09-04	A method for the direct manufacture of n-acyl derivatives of alpha-amino ypsilon-keto acids

Publications (1)

Publication Number	Publication Date
CA1077945A true CA1077945A (en)	1980-05-20

Family

ID=11048439

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA259,378A Expired CA1077945A (en)	1975-09-04	1976-08-18	Method for the direct manufacture of n-acyl derivatives of alpha-amino-gamma-keto acids and compounds thereof

Country Status (13)

Country	Link
JP (1)	JPS5233619A (da)
AU (1)	AU506345B2 (da)
BE (1)	BE845878A (da)
CA (1)	CA1077945A (da)
DE (1)	DE2639805A1 (da)
DK (1)	DK399676A (da)
ES (1)	ES450879A1 (da)
FR (1)	FR2322854A1 (da)
GB (1)	GB1547619A (da)
IL (1)	IL48047A0 (da)
LU (1)	LU75725A1 (da)
NL (1)	NL7609791A (da)
SE (1)	SE7609687L (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH021494A (ja) *	1988-03-31	1990-01-05	Yoshitomi Pharmaceut Ind Ltd	有機錫化合物の除去方法
CN115043753A (zh) *	2022-08-04	2022-09-13	东莞理工学院	一种以γ-戊内酯合成4-羟基戊酸酰胺的方法

1975
- 1975-09-04 IL IL48047A patent/IL48047A0/xx unknown
1976
- 1976-04-20 ES ES450879A patent/ES450879A1/es not_active Expired
- 1976-08-18 CA CA259,378A patent/CA1077945A/en not_active Expired
- 1976-08-25 AU AU17128/76A patent/AU506345B2/en not_active Expired
- 1976-09-02 SE SE7609687A patent/SE7609687L/xx unknown
- 1976-09-02 NL NL7609791A patent/NL7609791A/xx not_active Application Discontinuation
- 1976-09-02 GB GB36484/76A patent/GB1547619A/en not_active Expired
- 1976-09-03 DK DK399676A patent/DK399676A/da unknown
- 1976-09-03 DE DE19762639805 patent/DE2639805A1/de not_active Withdrawn
- 1976-09-03 LU LU75725A patent/LU75725A1/xx unknown
- 1976-09-03 FR FR7626678A patent/FR2322854A1/fr not_active Withdrawn
- 1976-09-04 JP JP51105446A patent/JPS5233619A/ja active Pending
- 1976-09-06 BE BE8000148A patent/BE845878A/xx unknown

Also Published As

Publication number	Publication date
NL7609791A (nl)	1977-03-08
DE2639805A1 (de)	1977-03-10
ES450879A1 (es)	1978-01-16
SE7609687L (sv)	1977-03-05
FR2322854A1 (fr)	1977-04-01
AU506345B2 (en)	1979-12-20
JPS5233619A (en)	1977-03-14
IL48047A0 (en)	1975-11-25
GB1547619A (en)	1979-06-27
DK399676A (da)	1977-03-05
AU1712876A (en)	1978-03-02
LU75725A1 (da)	1977-06-15
BE845878A (fr)	1976-12-31

Legal Events

Date	Code	Title	Description
1997-05-20	MKEX	Expiry

Publication	Publication Date	Title
Baciocchi et al.	1988	Synthesis of 3-acyl and 3-carboalkoxyfurans by the ceric ammonium nitrate promoted addition of 1, 3-dicarbonyl compounds to vinylic acetates
US3922307A (en)	1975-11-25	Process for preparing cyclohexanediones-(1,3)
US3932510A (en)	1976-01-13	Process for the preparation of cyclohexanediones-(1,3)
US3966813A (en)	1976-06-29	Process for the preparation of 1-(m- and p-hydroxyphenyl)-2-aminoethanol
Lebedev et al.	2005	Synthesis of 3-substituted arylpyrazole-4-carboxylic acids
Jones	1972	Preparation of 2-substituted indole sulfonamides and subsequent conversion to indole-2-carboxylic acids, indole-2-carbonitriles, and 2-acylindoles
Wheeler et al.	1987	Synthesis of 1-aminocyclopropenecarboxylic acid: the unsaturated analog of ACC
CA1077945A (en)	1980-05-20	Method for the direct manufacture of n-acyl derivatives of alpha-amino-gamma-keto acids and compounds thereof
Charrier et al.	1983	[1+ 3] Cycloadditions of isocyanides to azomethine ylides; synthesis and properties of 1-phthalimidoazetidines
HU195478B (en)	1988-05-30	Process for the production of azulene-derivatives
US3694466A (en)	1972-09-26	Process for the preparation of 2,5-dimethyl-4,5-dihydrofuran-3-ol-4-one
JP3221874B2 (ja)	2001-10-22	クラウセンアミドおよびネオクラウセンアミド並びにそれらの誘導体の製法
US4360691A (en)	1982-11-23	Production of malonic anhydrides and derivatives thereof
FR2370021A1 (fr)	1978-06-02	Procede pour la preparation de resorcinol ou de derives alkyl-substitues de ce produit
US4526985A (en)	1985-07-02	Process for the preparation of the anhydride of N-formyl-L-aspartic acid
Kollenz et al.	1973	SYNTHESIS OF 5-BENZOYL-6-PHENYL-1, 3-0XAZINONES+ (SYNTHESES OF HETEROCYCLES, 179.)
Jiricny et al.	1980	The conversion of aldehydes and ketones via their 2, 4, 6-tri-isopropylbenzenesulphonyl hydrazones into nitrites containing one additional carbon atom
US5130492A (en)	1992-07-14	Process for the production of squaric acid
Crawford et al.	1956	An improved synthesis of acetosyringone
US5905153A (en)	1999-05-18	Process for preparing (9α,13α,14α)-1-(3-methoxy-morphinan-17-yl)alkanones
Kataoka et al.	1995	Selective C S bond cleavage of 3-aryl-β-sultams with EtAlCl2
Baumgarten et al.	1971	Reactions of amines. XVII. Oxidation of. alpha.-substituted. alpha.-amino ketones with lead tetraacetate
Budnikova et al.	2001	Synthesis of endocyclic enol methyl ethers of 3-acylthiotetronic acids and their reactions with amines
US3059018A (en)	1962-10-16	Synthesis of esters of omega-cyanoalpha-oximino carboxylic acids
TSUJIKAWA et al.	1977	Studies on Heterocyclic Compounds. VI. Syntheses of Oudenone and Its Related Compounds.(1)