JPS6256144B2 - - Google Patents
Info
- Publication number
- JPS6256144B2 JPS6256144B2 JP1645978A JP1645978A JPS6256144B2 JP S6256144 B2 JPS6256144 B2 JP S6256144B2 JP 1645978 A JP1645978 A JP 1645978A JP 1645978 A JP1645978 A JP 1645978A JP S6256144 B2 JPS6256144 B2 JP S6256144B2
- Authority
- JP
- Japan
- Prior art keywords
- phenylglycine
- hydroxy
- group
- tert
- hydroxymethyl
- Prior art date
- 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
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 36
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 4
- UVDHSZPWPVHGKH-UHFFFAOYSA-N 2-acetamido-2-(3-hydroxyphenyl)acetic acid Chemical group CC(=O)NC(C(O)=O)C1=CC=CC(O)=C1 UVDHSZPWPVHGKH-UHFFFAOYSA-N 0.000 claims description 3
- XJYWPDFMPQMKPX-UHFFFAOYSA-N 2-benzamido-2-(3-hydroxyphenyl)acetic acid Chemical group C(C1=CC=CC=C1)(=O)NC(C1=CC(=CC=C1)O)C(=O)O XJYWPDFMPQMKPX-UHFFFAOYSA-N 0.000 claims description 3
- ULGJWNIHLSLQPZ-UHFFFAOYSA-N 7-[(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-yl)amino]-n-[2-(1h-indol-3-yl)ethyl]heptanamide Chemical compound C1CCCC2=NC3=CC(Cl)=CC(Cl)=C3C(NCCCCCCC(=O)NCCC=3C4=CC=CC=C4NC=3)=C21 ULGJWNIHLSLQPZ-UHFFFAOYSA-N 0.000 claims description 3
- 108010003977 aminoacylase I Proteins 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- KKLMJYDGZSAIQX-UHFFFAOYSA-N 2-(n-hydroxyanilino)acetic acid Chemical compound OC(=O)CN(O)C1=CC=CC=C1 KKLMJYDGZSAIQX-UHFFFAOYSA-N 0.000 claims 2
- OWZGHJNAVZKAIL-SNVBAGLBSA-N (2r)-2-(3-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical group CC(C)(C)OC(=O)N[C@@H](C(O)=O)C1=CC=CC(O)=C1 OWZGHJNAVZKAIL-SNVBAGLBSA-N 0.000 claims 1
- JRBXPUUAYKCCLQ-UHFFFAOYSA-N forphenicinol Chemical compound OC(=O)C(N)C1=CC=C(CO)C(O)=C1 JRBXPUUAYKCCLQ-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- -1 N-acetyl-3-hydroxyphenylglycine 3-Hydroxy-DL-phenylglycine Chemical compound 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000007031 hydroxymethylation reaction Methods 0.000 description 5
- OWZGHJNAVZKAIL-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)C1=CC=CC(O)=C1 OWZGHJNAVZKAIL-UHFFFAOYSA-N 0.000 description 4
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- YSRHMZBYTFKOCX-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)acetic acid Chemical compound C=1C=CC(O)=CC=1C(C(=O)O)NC(=O)OCC1=CC=CC=C1 YSRHMZBYTFKOCX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- TWGMQVBSQMTMCB-UHFFFAOYSA-N 2-acetamido-2-[3-hydroxy-4-(hydroxymethyl)phenyl]acetic acid Chemical compound CC(=O)NC(C(O)=O)C1=CC=C(CO)C(O)=C1 TWGMQVBSQMTMCB-UHFFFAOYSA-N 0.000 description 2
- DQLYTFPAEVJTFM-UHFFFAOYSA-N 2-azaniumyl-2-(3-hydroxyphenyl)acetate Chemical compound OC(=O)C(N)C1=CC=CC(O)=C1 DQLYTFPAEVJTFM-UHFFFAOYSA-N 0.000 description 2
- LSBIUXKNVUBKRI-UHFFFAOYSA-N 4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC=N1 LSBIUXKNVUBKRI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- TWGMQVBSQMTMCB-SNVBAGLBSA-N (2R)-2-acetamido-2-[3-hydroxy-4-(hydroxymethyl)phenyl]acetic acid Chemical compound C(C)(=O)N[C@H](C1=CC(=C(C=C1)CO)O)C(=O)O TWGMQVBSQMTMCB-SNVBAGLBSA-N 0.000 description 1
- JRBXPUUAYKCCLQ-MRVPVSSYSA-N (2r)-2-amino-2-[3-hydroxy-4-(hydroxymethyl)phenyl]acetic acid Chemical compound OC(=O)[C@H](N)C1=CC=C(CO)C(O)=C1 JRBXPUUAYKCCLQ-MRVPVSSYSA-N 0.000 description 1
- DQLYTFPAEVJTFM-SSDOTTSWSA-N (2r)-2-azaniumyl-2-(3-hydroxyphenyl)acetate Chemical compound OC(=O)[C@H](N)C1=CC=CC(O)=C1 DQLYTFPAEVJTFM-SSDOTTSWSA-N 0.000 description 1
- DQLYTFPAEVJTFM-ZETCQYMHSA-N (2s)-2-azaniumyl-2-(3-hydroxyphenyl)acetate Chemical compound OC(=O)[C@@H](N)C1=CC=CC(O)=C1 DQLYTFPAEVJTFM-ZETCQYMHSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- IVQDNDSBHMVGLM-UHFFFAOYSA-N 2-amino-2-[4-(hydroxymethyl)phenyl]acetic acid Chemical compound OC(=O)C(N)C1=CC=C(CO)C=C1 IVQDNDSBHMVGLM-UHFFFAOYSA-N 0.000 description 1
- NKFISLRONBSNFI-UHFFFAOYSA-N 2-benzamido-2-[3-hydroxy-4-(hydroxymethyl)phenyl]acetic acid Chemical compound C(C1=CC=CC=C1)(=O)NC(C1=CC(=C(C=C1)CO)O)C(=O)O NKFISLRONBSNFI-UHFFFAOYSA-N 0.000 description 1
- 241000589151 Azotobacter Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 150000005331 phenylglycines Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1645978A JPS54109943A (en) | 1978-02-17 | 1978-02-17 | Preparation of phenylglycine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1645978A JPS54109943A (en) | 1978-02-17 | 1978-02-17 | Preparation of phenylglycine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54109943A JPS54109943A (en) | 1979-08-29 |
| JPS6256144B2 true JPS6256144B2 (hu) | 1987-11-24 |
Family
ID=11916823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1645978A Granted JPS54109943A (en) | 1978-02-17 | 1978-02-17 | Preparation of phenylglycine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54109943A (hu) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1731849A4 (en) | 2003-12-10 | 2013-09-18 | Panasonic Corp | HEAT EXCHANGER AND CLEANING DEVICE THEREFOR |
| US8731386B2 (en) | 2011-09-30 | 2014-05-20 | Borgwarner Beru Systems Gmbh | Electric heating device for heating fluids |
| DE202011107227U1 (de) | 2011-10-28 | 2011-11-09 | Türk & Hillinger GmbH | Durchlauferhitzer |
-
1978
- 1978-02-17 JP JP1645978A patent/JPS54109943A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54109943A (en) | 1979-08-29 |
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