IE50915B1

IE50915B1 - Branched amides of l-aspartyl-d-amino acid dipeptides and compositions thereof

Branched amides of l-aspartyl-d-amino acid dipeptides and compositions thereof

Info

Publication number: IE50915B1
Authority: IE; Ireland
Prior art keywords: methyl; ethyl; hydrogen; amide; formula
Prior art date: 1980-01-21

Application number

IE92/81A

Other languages

English (en)

Other versions

IE810092L (en

Original Assignee

Pfizer

Priority date

1980-01-21

Filing date

1981-01-20

Publication date

1986-08-20

1980-11-05 Priority claimed from US06/201,745 external-priority patent/US4411925A/en

1981-01-20 Application filed by Pfizer filed Critical Pfizer

1981-07-21 Publication of IE810092L publication Critical patent/IE810092L/xx

1986-08-20 Publication of IE50915B1 publication Critical patent/IE50915B1/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 261
150000001408 amides Chemical class 0.000 title claims abstract description 121
-1 l-aspartyl-d-amino Chemical group 0.000 title claims abstract description 68
108010016626 Dipeptides Proteins 0.000 title claims abstract description 53
238000000034 method Methods 0.000 claims abstract description 124
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 80
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 53
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 49
239000001257 hydrogen Substances 0.000 claims abstract description 48
125000000217 alkyl group Chemical group 0.000 claims abstract description 40
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 32
239000002253 acid Substances 0.000 claims abstract description 30
150000003839 salts Chemical class 0.000 claims abstract description 20
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 14
125000002091 cationic group Chemical group 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
238000004519 manufacturing process Methods 0.000 claims abstract description 3
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 158
150000001875 compounds Chemical class 0.000 claims description 108
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 68
239000002904 solvent Substances 0.000 claims description 64
238000006243 chemical reaction Methods 0.000 claims description 50
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 33
DVUFTQLHHHJEMK-DMTCNVIQSA-N (3s)-3-amino-4-[[(1r)-1-carboxyethyl]amino]-4-oxobutanoic acid Chemical compound OC(=O)[C@@H](C)NC(=O)[C@@H](N)CC(O)=O DVUFTQLHHHJEMK-DMTCNVIQSA-N 0.000 claims description 32
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 28
229940081974 saccharin Drugs 0.000 claims description 21
235000019204 saccharin Nutrition 0.000 claims description 21
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 21
125000006239 protecting group Chemical group 0.000 claims description 19
229940024606 amino acid Drugs 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
239000000463 material Substances 0.000 claims description 14
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 13
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
229960005261 aspartic acid Drugs 0.000 claims description 12
150000008574 D-amino acids Chemical class 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 9
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 4
235000014171 carbonated beverage Nutrition 0.000 claims description 2
150000003141 primary amines Chemical class 0.000 claims description 2
MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims 5
BTIIGNUPPKUQAP-UHFFFAOYSA-N [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;diperchlorate Chemical compound [O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 BTIIGNUPPKUQAP-UHFFFAOYSA-N 0.000 claims 3
WTMBKQSWYNWDFS-HEYAKCRZSA-N N[C@@H](CC(O)=O)C(=O)N[C@H](C)C(=O)O.CC1(SCC(C1NC([C@H](NC([C@@H](N)CC(O)=O)=O)C)=O)(C)C)C Chemical compound N[C@@H](CC(O)=O)C(=O)N[C@H](C)C(=O)O.CC1(SCC(C1NC([C@H](NC([C@@H](N)CC(O)=O)=O)C)=O)(C)C)C WTMBKQSWYNWDFS-HEYAKCRZSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 abstract description 59
235000003599 food sweetener Nutrition 0.000 abstract description 27
239000003765 sweetening agent Substances 0.000 abstract description 27
150000007513 acids Chemical class 0.000 abstract description 4
229910052717 sulfur Inorganic materials 0.000 abstract description 4
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 abstract description 3
229910052760 oxygen Inorganic materials 0.000 abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 221
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 168
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 165
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 165
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 155
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 117
239000000243 solution Substances 0.000 description 114
239000000047 product Substances 0.000 description 93
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 91
150000002576 ketones Chemical class 0.000 description 73
239000000284 extract Substances 0.000 description 51
229930006000 Sucrose Natural products 0.000 description 47
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 47
239000005720 sucrose Substances 0.000 description 47
238000010992 reflux Methods 0.000 description 46
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
239000011541 reaction mixture Substances 0.000 description 42
239000007787 solid Substances 0.000 description 42
239000000543 intermediate Substances 0.000 description 41
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
238000001914 filtration Methods 0.000 description 31
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
230000002829 reductive effect Effects 0.000 description 28
238000003756 stirring Methods 0.000 description 27
239000012267 brine Substances 0.000 description 26
239000003054 catalyst Substances 0.000 description 26
238000004809 thin layer chromatography Methods 0.000 description 24
150000002923 oximes Chemical class 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
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 22
239000011734 sodium Substances 0.000 description 22
229910052708 sodium Inorganic materials 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
238000001704 evaporation Methods 0.000 description 21
230000008020 evaporation Effects 0.000 description 21
239000012044 organic layer Substances 0.000 description 21
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
238000002360 preparation method Methods 0.000 description 20
239000000741 silica gel Substances 0.000 description 20
229910002027 silica gel Inorganic materials 0.000 description 20
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 19
229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
235000017557 sodium bicarbonate Nutrition 0.000 description 19
229960001407 sodium bicarbonate Drugs 0.000 description 19
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
239000003921 oil Substances 0.000 description 17
235000019198 oils Nutrition 0.000 description 17
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
239000008346 aqueous phase Substances 0.000 description 16
239000007788 liquid Substances 0.000 description 16
230000036515 potency Effects 0.000 description 15
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
238000007327 hydrogenolysis reaction Methods 0.000 description 14
239000004615 ingredient Substances 0.000 description 14
235000009508 confectionery Nutrition 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 12
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
150000008064 anhydrides Chemical class 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
230000007062 hydrolysis Effects 0.000 description 12
238000006460 hydrolysis reaction Methods 0.000 description 12
239000010410 layer Substances 0.000 description 12
235000019341 magnesium sulphate Nutrition 0.000 description 12
QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 11
239000000843 powder Substances 0.000 description 11
239000007921 spray Substances 0.000 description 11
150000003462 sulfoxides Chemical class 0.000 description 11
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 10
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
235000013361 beverage Nutrition 0.000 description 10
235000015165 citric acid Nutrition 0.000 description 10
235000019253 formic acid Nutrition 0.000 description 10
238000006722 reduction reaction Methods 0.000 description 10
QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
229910052740 iodine Inorganic materials 0.000 description 9
150000003457 sulfones Chemical class 0.000 description 9
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
238000001035 drying Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
235000013305 food Nutrition 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000000725 suspension Substances 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 7
230000008878 coupling Effects 0.000 description 7
238000010168 coupling process Methods 0.000 description 7
238000005859 coupling reaction Methods 0.000 description 7
239000000796 flavoring agent Substances 0.000 description 7
229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000002002 slurry Substances 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 6
239000007832 Na2SO4 Substances 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
150000001413 amino acids Chemical group 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
239000002585 base Substances 0.000 description 6
235000012970 cakes Nutrition 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
239000012043 crude product Substances 0.000 description 6
235000019634 flavors Nutrition 0.000 description 6
239000002243 precursor Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
235000019640 taste Nutrition 0.000 description 6
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 6
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 6
235000012141 vanillin Nutrition 0.000 description 6
238000005406 washing Methods 0.000 description 6
101100421901 Caenorhabditis elegans sos-1 gene Proteins 0.000 description 5
229920001100 Polydextrose Polymers 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
235000001014 amino acid Nutrition 0.000 description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
125000000896 monocarboxylic acid group Chemical group 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
239000001259 polydextrose Substances 0.000 description 5
235000013856 polydextrose Nutrition 0.000 description 5
229940035035 polydextrose Drugs 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
238000010561 standard procedure Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000006188 syrup Substances 0.000 description 5
235000020357 syrup Nutrition 0.000 description 5
TYRGLVWXHJRKMT-MRVPVSSYSA-N (2r)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound OC(=O)[C@@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-MRVPVSSYSA-N 0.000 description 4
KNIZBZYMVRWQKN-DMTCNVIQSA-N (3s)-3-amino-4-[[(2r)-1-amino-1-oxopropan-2-yl]amino]-4-oxobutanoic acid Chemical class NC(=O)[C@@H](C)NC(=O)[C@@H](N)CC(O)=O KNIZBZYMVRWQKN-DMTCNVIQSA-N 0.000 description 4
WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 4
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
239000005695 Ammonium acetate Substances 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
KZSNJWFQEVHDMF-SCSAIBSYSA-N D-valine Chemical compound CC(C)[C@@H](N)C(O)=O KZSNJWFQEVHDMF-SCSAIBSYSA-N 0.000 description 4
229930182831 D-valine Natural products 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
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