CA1285282C - Amides substitues par des groupes thietanyles - Google Patents

Amides substitues par des groupes thietanyles

Info

Publication number: CA1285282C
Authority: CA; Canada
Prior art keywords: carbon atoms; compound according; alkyl; amino; thietanyl
Prior art date: 1986-06-18
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 - Lifetime

Application number

CA000542196A

Other languages

English (en)

Inventor

Paul R. Zanno

Glenn M. Roy

Ronald E. Barnett

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.)

Mondelez International Inc

General Foods Corp

Original Assignee

General Foods Corp

Kraft General Foods Inc

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.)

1986-06-18

Filing date

1987-07-15

Publication date

1991-06-25

1986-06-18 Priority claimed from US06/875,854 external-priority patent/US4758443A/en

1987-07-15 Application filed by General Foods Corp, Kraft General Foods Inc filed Critical General Foods Corp

1987-07-15 Priority to CA000542196A priority Critical patent/CA1285282C/fr

1991-06-25 Application granted granted Critical

1991-06-25 Publication of CA1285282C publication Critical patent/CA1285282C/fr

2008-06-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001408 amides Chemical class 0.000 title description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 94
235000003599 food sweetener Nutrition 0.000 claims abstract description 50
125000000217 alkyl group Chemical group 0.000 claims abstract description 41
239000001257 hydrogen Substances 0.000 claims abstract description 29
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
125000002053 thietanyl group Chemical group 0.000 claims abstract description 28
125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
235000013305 food Nutrition 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 19
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052799 carbon Inorganic materials 0.000 claims abstract description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
150000002431 hydrogen Chemical class 0.000 claims abstract description 12
125000004849 alkoxymethyl group Chemical group 0.000 claims abstract description 11
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 11
125000006239 protecting group Chemical group 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 87
-1 tetramethylthietanyl Chemical group 0.000 claims description 73
239000003765 sweetening agent Substances 0.000 claims description 49
239000000203 mixture Substances 0.000 claims description 34
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 19
108010016626 Dipeptides Proteins 0.000 claims description 18
239000007787 solid Substances 0.000 claims description 18
239000001273 butane Substances 0.000 claims description 17
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 17
229930006000 Sucrose Natural products 0.000 claims description 8
239000005720 sucrose Substances 0.000 claims description 8
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
239000006188 syrup Substances 0.000 claims description 5
235000020357 syrup Nutrition 0.000 claims description 5
IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims description 4
108010011485 Aspartame Proteins 0.000 claims description 4
239000000605 aspartame Substances 0.000 claims description 4
235000010357 aspartame Nutrition 0.000 claims description 4
229960003438 aspartame Drugs 0.000 claims description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 3
235000013361 beverage Nutrition 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
229940109275 cyclamate Drugs 0.000 claims description 3
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 3
239000008121 dextrose Substances 0.000 claims description 3
QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 claims description 3
PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
229930091371 Fructose Natural products 0.000 claims description 2
239000005715 Fructose Substances 0.000 claims description 2
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
239000004378 Glycyrrhizin Substances 0.000 claims description 2
229930195725 Mannitol Natural products 0.000 claims description 2
UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 claims description 2
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
240000008042 Zea mays Species 0.000 claims description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
125000006242 amine protecting group Chemical group 0.000 claims description 2
235000005822 corn Nutrition 0.000 claims description 2
235000011852 gelatine desserts Nutrition 0.000 claims description 2
150000002303 glucose derivatives Chemical class 0.000 claims description 2
LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 claims description 2
229960004949 glycyrrhizic acid Drugs 0.000 claims description 2
UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims description 2
235000019410 glycyrrhizin Nutrition 0.000 claims description 2
LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 claims description 2
239000000594 mannitol Substances 0.000 claims description 2
235000010355 mannitol Nutrition 0.000 claims description 2
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
239000000600 sorbitol Substances 0.000 claims description 2
235000010356 sorbitol Nutrition 0.000 claims description 2
229940013618 stevioside Drugs 0.000 claims description 2
OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 claims description 2
235000019202 steviosides Nutrition 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
239000000811 xylitol Substances 0.000 claims description 2
235000010447 xylitol Nutrition 0.000 claims description 2
229960002675 xylitol Drugs 0.000 claims description 2
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
229910006069 SO3H Inorganic materials 0.000 claims 2
125000001475 halogen functional group Chemical group 0.000 claims 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims 2
NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims 1
229960004050 aminobenzoic acid Drugs 0.000 claims 1
229960001031 glucose Drugs 0.000 claims 1
229960001855 mannitol Drugs 0.000 claims 1
239000008267 milk Substances 0.000 claims 1
210000004080 milk Anatomy 0.000 claims 1
235000013336 milk Nutrition 0.000 claims 1
229960002920 sorbitol Drugs 0.000 claims 1
125000000185 sucrose group Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
239000004321 EU approved sweetener Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 0.000 description 27
239000000243 solution Substances 0.000 description 27
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
238000000034 method Methods 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
229910052786 argon Inorganic materials 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
239000002253 acid Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
229960005261 aspartic acid Drugs 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 8
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
150000001721 carbon Chemical group 0.000 description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000008122 artificial sweetener Substances 0.000 description 6
235000021311 artificial sweeteners Nutrition 0.000 description 6
229960004132 diethyl ether Drugs 0.000 description 6
238000001914 filtration Methods 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
235000019605 sweet taste sensations Nutrition 0.000 description 6
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
235000019640 taste Nutrition 0.000 description 5
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000002390 rotary evaporation Methods 0.000 description 4
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
235000019204 saccharin Nutrition 0.000 description 4
229940081974 saccharin Drugs 0.000 description 4
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
GWKOSRIHVSBBIA-REOHCLBHSA-N (3s)-3-aminooxolane-2,5-dione Chemical compound N[C@H]1CC(=O)OC1=O GWKOSRIHVSBBIA-REOHCLBHSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
206010013911 Dysgeusia Diseases 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
235000003704 aspartic acid Nutrition 0.000 description 3
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
235000011850 desserts Nutrition 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
235000021096 natural sweeteners Nutrition 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000006072 paste Substances 0.000 description 3
230000001953 sensory effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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 2
UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
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Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Seasonings (AREA)
Peptides Or Proteins (AREA)

CA000542196A 1986-06-18 1987-07-15 Amides substitues par des groupes thietanyles Expired - Lifetime CA1285282C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000542196A CA1285282C (fr)	1986-06-18	1987-07-15	Amides substitues par des groupes thietanyles

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/875,854 US4758443A (en)	1986-06-18	1986-06-18	Thietanyl-substituted amides and use thereof as sweeteners
CA000542196A CA1285282C (fr)	1986-06-18	1987-07-15	Amides substitues par des groupes thietanyles

Publications (1)

Publication Number	Publication Date
CA1285282C true CA1285282C (fr)	1991-06-25

Family

ID=25671424

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000542196A Expired - Lifetime CA1285282C (fr)	1986-06-18	1987-07-15	Amides substitues par des groupes thietanyles

Country Status (1)

Country	Link
CA (1)	CA1285282C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115093391A (zh) *	2022-06-28	2022-09-23	上海毕得医药科技股份有限公司	一种3-硫杂环丁胺盐酸盐的合成方法

1987
- 1987-07-15 CA CA000542196A patent/CA1285282C/fr not_active Expired - Lifetime

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115093391A (zh) *	2022-06-28	2022-09-23	上海毕得医药科技股份有限公司	一种3-硫杂环丁胺盐酸盐的合成方法
CN115093391B (zh) *	2022-06-28	2024-05-03	上海毕得医药科技股份有限公司	一种3-硫杂环丁胺盐酸盐的合成方法

Legal Events

Date	Code	Title	Description
1995-12-25	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 19951225

Publication	Publication Date	Title
US4619834A (en)	1986-10-28	Sweetening with L-aminodicarboxylic acid aminoalkenoic acid ester amides
US4636396A (en)	1987-01-13	Foodstuff with L-aminodicarboxylic acid gem-diamines
US4634792A (en)	1987-01-06	L-aminodicarboxylic acid aminoalkenoic acid ester amides
US4652457A (en)	1987-03-24	L-aminodicarboxylic acid aminoalkenoic acid ester amides
US4638071A (en)	1987-01-20	Cycloalkyl ethers and thioethers of dipeptides
US4571308A (en)	1986-02-18	L-Aminodicarboxylic acid aminoalkenoic acid ester amides
US4572799A (en)	1986-02-25	L-Aminodicarboxylic acid amides
US4654439A (en)	1987-03-31	L-aminodicarboxylic acid amides of alkoxyalkylamines
US4622418A (en)	1986-11-11	L-aminodicarboxylic acid amides
US4652676A (en)	1987-03-24	L-aminodicarboxylic acid alkenes
US4758443A (en)	1988-07-19	Thietanyl-substituted amides and use thereof as sweeteners
US4654219A (en)	1987-03-31	L-aminodicarboxylic-(O-cycloalkyl)-L-aminocarboxylate alkyl ester sweeteners
US4650688A (en)	1987-03-17	Sweetening with L-aminodicarboxylic acid amides of alkoxyalkylamines
US4822635A (en)	1989-04-18	Sweetening with L-aminodicarboxylic acid esters
US4622232A (en)	1986-11-11	L-aminodicarboxylic acid alkanes
US4701552A (en)	1987-10-20	L-aminodicarboxylic acid alkanes
US4603012A (en)	1986-07-29	L-aminodicarboxylic acid alkanes
US4676989A (en)	1987-06-30	Sweetening with cycloalkyl ethers and thioethers of dipeptides
CA1285282C (fr)	1991-06-25	Amides substitues par des groupes thietanyles
US4781927A (en)	1988-11-01	Sweetening with l-aminodicarboxylic acid esters
US4678674A (en)	1987-07-07	Sweetening with L-aminodicarboxylic acid amides
US4788073A (en)	1988-11-29	Sweetening with L-aminodicarboxylic acid alkenes
US4678675A (en)	1987-07-07	Sweetening with L-aminodicarboxylic acid alkenes
US4603011A (en)	1986-07-29	L-aminodicarboxylic acid amides of alkoxyalkylamines
US4788332A (en)	1988-11-29	L-aminodicarboxylic acid esters