CH340506A - Procédé de préparation d'un dérivé tribromé de la série du prégnane - Google Patents

Procédé de préparation d'un dérivé tribromé de la série du prégnane

Info

Publication number: CH340506A
Authority: CH; Switzerland
Prior art keywords: pregnane; trione; hydroxy; bromine; preparation
Prior art date: 1955-06-24

Application number

Other languages

English (en)

French (fr)

Inventor

Joly Robert

Nomine Gerard

Bertin Daniel

Original Assignee

Chimiotherapie Lab Franc

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.)

1955-06-24

Filing date

1956-04-12

Publication date

1959-08-31

1956-04-12 Application filed by Chimiotherapie Lab Franc filed Critical Chimiotherapie Lab Franc

1959-08-31 Publication of CH340506A publication Critical patent/CH340506A/de

Links

238000002360 preparation method Methods 0.000 title claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
230000031709 bromination Effects 0.000 claims description 6
238000005893 bromination reaction Methods 0.000 claims description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
150000003128 pregnanes Chemical class 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
-1 bromo compound Chemical class 0.000 claims description 2
238000001640 fractional crystallisation Methods 0.000 claims description 2
239000001632 sodium acetate Substances 0.000 claims description 2
235000017281 sodium acetate Nutrition 0.000 claims description 2
SEYZXAVWOGPELQ-AGIMVQGUSA-N (8S,9S,10S,13S,14S,17R)-17-(2-bromoacetyl)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,11-dione Chemical compound BrCC([C@]1(CC[C@H]2[C@@H]3CCC4CC(CC[C@]4(C)[C@H]3C(C[C@]12C)=O)=O)O)=O SEYZXAVWOGPELQ-AGIMVQGUSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000004289 sodium hydrogen sulphite Substances 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
238000005406 washing Methods 0.000 description 2
VOKCXZLJZWUHJS-SIJLRWKYSA-N (8S,9S,10R,13S,14S,17R)-2,4-dibromo-17-(2-bromoacetyl)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,11-dione Chemical compound BrC1C(C(C2CC[C@H]3[C@@H]4CC[C@](C(CBr)=O)([C@]4(CC([C@@H]3[C@]2(C1)C)=O)C)O)Br)=O VOKCXZLJZWUHJS-SIJLRWKYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

CH340506D 1955-06-24 1956-04-12 Procédé de préparation d'un dérivé tribromé de la série du prégnane CH340506A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR340506X		1955-06-24

Publications (1)

Publication Number	Publication Date
CH340506A true CH340506A (de)	1959-08-31

Family

ID=8891805

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH340506D CH340506A (de)	1955-06-24	1956-04-12	Procédé de préparation d'un dérivé tribromé de la série du prégnane

Country Status (1)

Country	Link
CH (1)	CH340506A (de)

1956
- 1956-04-12 CH CH340506D patent/CH340506A/de unknown

Publication	Publication Date	Title
CN111333494A (zh)	2020-06-26	6-甲氧基-1-萘满酮的合成方法
CH340506A (de)	1959-08-31	Procédé de préparation d'un dérivé tribromé de la série du prégnane
US3012073A (en)	1961-12-05	Trifluoro methylthiophenyl-dichloro-acet-amides-1, 3-propanediol
Reimer	1931	Benzalpyruvic acid dibromide
Whitmore et al.	1941	Studies on Hexamethylethane and Related Compounds
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CH432512A (fr)	1967-03-31	Procédé de préparation de stéroïdes 21-bromés
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SU376380A1 (ru)	1973-04-05	Способ получения
Kohler et al.	1919	The Bromination and Bromine Derivatives of Certain δ-KETONIC Esters.
BE876900A (fr)	1979-10-01	Procede de production de pyrrolidine-2-ones a partir de 3-pyrroline-2-ones et de production de 3-pyrroline-2-ones
BE549904A (de)
Reimer et al.	1941	Certain reactions of p-bromocinnamic acid
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Noller et al.	1956	Synthesis of the Racemic p-Dimethylaminobenzylidene-N, N'-bis-(1-phenylethyl)-malonamides
BE443192A (de)
BE540075A (de)	1955-08-13
SE185447C1 (de)	1963-01-01
BE640360A (de)