JPS6155499B2 - - Google Patents
Info
- Publication number
- JPS6155499B2 JPS6155499B2 JP53148591A JP14859178A JPS6155499B2 JP S6155499 B2 JPS6155499 B2 JP S6155499B2 JP 53148591 A JP53148591 A JP 53148591A JP 14859178 A JP14859178 A JP 14859178A JP S6155499 B2 JPS6155499 B2 JP S6155499B2
- Authority
- JP
- Japan
- Prior art keywords
- benzoylaminoisobutyronitrile
- acid
- alkaline
- mixtures
- hydroxide
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 4
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QCHPKSFMDHPSNR-UHFFFAOYSA-N 3-aminoisobutyric acid Chemical compound NCC(C)C(O)=O QCHPKSFMDHPSNR-UHFFFAOYSA-N 0.000 description 6
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 5
- JDEFPFLTCXIVDH-UHFFFAOYSA-N 2-cyanopropanoic acid Chemical compound N#CC(C)C(O)=O JDEFPFLTCXIVDH-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
- AXAMLHJXUICVAY-UHFFFAOYSA-N 2-benzamido-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC(=O)C1=CC=CC=C1 AXAMLHJXUICVAY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- -1 triamcinolone acetonide ester Chemical class 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT52004/77A IT1116382B (it) | 1977-11-30 | 1977-11-30 | Metodo di preparazione industriale dell'acido rs-beta-benzoilamino isobutirrico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5484542A JPS5484542A (en) | 1979-07-05 |
| JPS6155499B2 true JPS6155499B2 (en, 2012) | 1986-11-28 |
Family
ID=11276181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14859178A Granted JPS5484542A (en) | 1977-11-30 | 1978-11-30 | Method of manufacturing d*11betaabenzoyl aminoisoethylacetic acid |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4335256A (en, 2012) |
| JP (1) | JPS5484542A (en, 2012) |
| AT (1) | AT362769B (en, 2012) |
| AU (1) | AU520597B2 (en, 2012) |
| BE (1) | BE872139A (en, 2012) |
| CA (1) | CA1107757A (en, 2012) |
| CH (1) | CH636850A5 (en, 2012) |
| DE (1) | DE2851427A1 (en, 2012) |
| DK (1) | DK149197C (en, 2012) |
| ES (1) | ES475359A1 (en, 2012) |
| FR (1) | FR2410643A1 (en, 2012) |
| GB (1) | GB2009176B (en, 2012) |
| GR (1) | GR65322B (en, 2012) |
| IE (1) | IE47564B1 (en, 2012) |
| IT (1) | IT1116382B (en, 2012) |
| LU (1) | LU80602A1 (en, 2012) |
| NL (1) | NL185076C (en, 2012) |
| NO (1) | NO148885C (en, 2012) |
| PT (1) | PT68816A (en, 2012) |
| SE (1) | SE431448B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE32952E (en) * | 1986-05-19 | 1989-06-13 | Minnesota Mining And Manufacturing Company | Method of preparing N-acryloyl-α-amino acids |
| US4694103A (en) * | 1986-05-19 | 1987-09-15 | Minnesota Mining And Manufacturing Company | Method of preparing N-acryloyl-α-amino acids |
| GB9520092D0 (en) * | 1995-10-02 | 1995-12-06 | Hoechst Roussel Ltd | Chemical compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2461842A (en) * | 1943-02-26 | 1949-02-15 | Sharples Chemicals Inc | Condensation of nitriles with amides and the production of beta-alanine |
| US2510784A (en) * | 1949-01-13 | 1950-06-06 | Sterling Drug Inc | Bis (tertiaryaminoalkyl) arylacetonitriles and the corresponding acids and esters |
| US2849477A (en) * | 1956-06-12 | 1958-08-26 | Dornow Alfred | Preparation of alpha-acylamino-nitriles |
| US3489793A (en) * | 1966-05-16 | 1970-01-13 | Francia Formaceutici S R L | New benzamido butyric acid derivatives |
-
1977
- 1977-11-30 IT IT52004/77A patent/IT1116382B/it active
-
1978
- 1978-11-15 IE IE2253/78A patent/IE47564B1/en unknown
- 1978-11-16 US US05/961,102 patent/US4335256A/en not_active Expired - Lifetime
- 1978-11-16 FR FR7832358A patent/FR2410643A1/fr active Granted
- 1978-11-17 AU AU41670/78A patent/AU520597B2/en not_active Expired
- 1978-11-20 BE BE191829A patent/BE872139A/xx not_active IP Right Cessation
- 1978-11-22 PT PT68816A patent/PT68816A/pt unknown
- 1978-11-24 GB GB7846062A patent/GB2009176B/en not_active Expired
- 1978-11-24 ES ES475359A patent/ES475359A1/es not_active Expired
- 1978-11-27 AT AT0847278A patent/AT362769B/de not_active IP Right Cessation
- 1978-11-28 NL NLAANVRAGE7811674,A patent/NL185076C/xx not_active IP Right Cessation
- 1978-11-28 DE DE19782851427 patent/DE2851427A1/de active Granted
- 1978-11-28 SE SE7812247A patent/SE431448B/sv not_active IP Right Cessation
- 1978-11-28 GR GR57750A patent/GR65322B/el unknown
- 1978-11-29 CH CH1222378A patent/CH636850A5/it not_active IP Right Cessation
- 1978-11-29 DK DK534278A patent/DK149197C/da not_active IP Right Cessation
- 1978-11-29 NO NO784014A patent/NO148885C/no unknown
- 1978-11-29 CA CA317,049A patent/CA1107757A/en not_active Expired
- 1978-11-30 LU LU80602A patent/LU80602A1/xx unknown
- 1978-11-30 JP JP14859178A patent/JPS5484542A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NO784014L (no) | 1979-05-31 |
| DE2851427A1 (de) | 1979-05-31 |
| JPS5484542A (en) | 1979-07-05 |
| NL185076B (nl) | 1989-08-16 |
| GB2009176A (en) | 1979-06-13 |
| US4335256A (en) | 1982-06-15 |
| ES475359A1 (es) | 1979-04-01 |
| NL7811674A (nl) | 1979-06-01 |
| NL185076C (nl) | 1990-01-16 |
| CH636850A5 (it) | 1983-06-30 |
| DK149197C (da) | 1986-08-11 |
| BE872139A (fr) | 1979-03-16 |
| FR2410643A1 (fr) | 1979-06-29 |
| IE47564B1 (en) | 1984-04-18 |
| AT362769B (de) | 1981-06-10 |
| SE7812247L (sv) | 1979-05-31 |
| CA1107757A (en) | 1981-08-25 |
| FR2410643B1 (en, 2012) | 1983-12-23 |
| NO148885C (no) | 1984-01-04 |
| GR65322B (en) | 1980-08-11 |
| DE2851427C2 (en, 2012) | 1987-12-03 |
| PT68816A (en) | 1978-12-01 |
| GB2009176B (en) | 1982-02-24 |
| NO148885B (no) | 1983-09-26 |
| SE431448B (sv) | 1984-02-06 |
| ATA847278A (de) | 1980-11-15 |
| DK534278A (da) | 1979-05-31 |
| DK149197B (da) | 1986-03-10 |
| LU80602A1 (fr) | 1979-03-22 |
| IE782253L (en) | 1979-05-30 |
| AU4167078A (en) | 1979-06-07 |
| AU520597B2 (en) | 1982-02-11 |
| IT1116382B (it) | 1986-02-10 |
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