FR2376838A1 - Alpha-acylamino-crotonic and butyric acid derivs. - intermediates for direct synthesis of D-2-amino-butanol which is a precursor for ethambutol - Google Patents
Alpha-acylamino-crotonic and butyric acid derivs. - intermediates for direct synthesis of D-2-amino-butanol which is a precursor for ethambutolInfo
- Publication number
- FR2376838A1 FR2376838A1 FR7800252A FR7800252A FR2376838A1 FR 2376838 A1 FR2376838 A1 FR 2376838A1 FR 7800252 A FR7800252 A FR 7800252A FR 7800252 A FR7800252 A FR 7800252A FR 2376838 A1 FR2376838 A1 FR 2376838A1
- Authority
- FR
- France
- Prior art keywords
- ethambutol
- intermediates
- amino
- direct synthesis
- acylamino
- 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.)
- Pending
Links
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 title abstract 4
- 239000000543 intermediate Substances 0.000 title abstract 3
- JCBPETKZIGVZRE-BYPYZUCNSA-N (2s)-2-aminobutan-1-ol Chemical compound CC[C@H](N)CO JCBPETKZIGVZRE-BYPYZUCNSA-N 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 229960000285 ethambutol Drugs 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 title 2
- 239000002243 precursor Substances 0.000 title 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- -1 methoxy, phenoxy Chemical group 0.000 abstract 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Amides of formulae (CH3CH=C(R1)NHCOR2(III) and CH3CH2C(R1)HNHCOR2 (IV) are new. In the formulae, R1 is COOH or 2-7C alkoxycarbonyl; and R2 is H, 1-6C alkyl, phenyl (opt. substd. by halo or 1-3C alkyl), amino (opt. substd. by 1-6C alkyl), amido, 1-6C alkoxy, phenoxy (opt. substd. as phenyl) or 2-7C alkoxycarbonyl. Esp. pref. cpds. have R2=H, CH3, isopropyl, phenyl, NH2, amid, methoxy, phenoxy or carbomethoxy. Amides are intermediates in a direct synthesis of d-2-aminobutanol (I) which avoids the need for a resolution stage and recycling of the unwanted isomer. (I) is an intermediate for ethambutol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75753577A | 1977-01-07 | 1977-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2376838A1 true FR2376838A1 (en) | 1978-08-04 |
Family
ID=25048189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7800252A Pending FR2376838A1 (en) | 1977-01-07 | 1978-01-05 | Alpha-acylamino-crotonic and butyric acid derivs. - intermediates for direct synthesis of D-2-amino-butanol which is a precursor for ethambutol |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5387311A (en) |
| AU (1) | AU3217278A (en) |
| BE (1) | BE862627A (en) |
| DE (1) | DE2800461A1 (en) |
| ES (1) | ES465790A1 (en) |
| FR (1) | FR2376838A1 (en) |
| IT (1) | IT1104135B (en) |
| NL (1) | NL7800209A (en) |
| PL (1) | PL203860A1 (en) |
| ZA (1) | ZA777252B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA793744B (en) * | 1978-07-24 | 1981-02-25 | Merck & Co Inc | Z-2-acylamino-3-monsosubstituted propenoates |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2160413A (en) * | 1935-04-16 | 1939-05-30 | Schering Ag | Polyiodo derivatives of acylamino acids and their salts and a method of making the same |
| US2394230A (en) * | 1941-09-19 | 1946-02-05 | John H Billman | Methods of preparing alpha-amino acids and nu-substituted-alpha-amino acids |
| DE1137019B (en) * | 1958-12-03 | 1962-09-27 | Lentia Gmbh | Process for the preparation of four or five times iodinated benzoic acid esters or amides |
| GB1349895A (en) * | 1971-05-26 | 1974-04-10 | Monsanto Co | Catalytic asymmetric hydrogenation |
-
1976
- 1976-12-06 ZA ZA777252A patent/ZA777252B/en unknown
-
1978
- 1978-01-04 AU AU32172/78A patent/AU3217278A/en active Pending
- 1978-01-04 BE BE184093A patent/BE862627A/en unknown
- 1978-01-05 DE DE19782800461 patent/DE2800461A1/en not_active Withdrawn
- 1978-01-05 ES ES465790A patent/ES465790A1/en not_active Expired
- 1978-01-05 FR FR7800252A patent/FR2376838A1/en active Pending
- 1978-01-06 NL NL7800209A patent/NL7800209A/en not_active Application Discontinuation
- 1978-01-06 IT IT47551/78A patent/IT1104135B/en active
- 1978-01-06 PL PL20386078A patent/PL203860A1/en unknown
- 1978-01-07 JP JP39778A patent/JPS5387311A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2160413A (en) * | 1935-04-16 | 1939-05-30 | Schering Ag | Polyiodo derivatives of acylamino acids and their salts and a method of making the same |
| US2394230A (en) * | 1941-09-19 | 1946-02-05 | John H Billman | Methods of preparing alpha-amino acids and nu-substituted-alpha-amino acids |
| DE1137019B (en) * | 1958-12-03 | 1962-09-27 | Lentia Gmbh | Process for the preparation of four or five times iodinated benzoic acid esters or amides |
| GB1349895A (en) * | 1971-05-26 | 1974-04-10 | Monsanto Co | Catalytic asymmetric hydrogenation |
Non-Patent Citations (4)
| Title |
|---|
| EXBK/22 * |
| EXBK/29 * |
| EXBK/63 * |
| EXBK/72 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES465790A1 (en) | 1979-01-01 |
| DE2800461A1 (en) | 1978-07-13 |
| JPS5387311A (en) | 1978-08-01 |
| IT7847551A0 (en) | 1978-01-06 |
| ZA777252B (en) | 1977-12-28 |
| PL203860A1 (en) | 1979-08-13 |
| AU3217278A (en) | 1979-07-12 |
| BE862627A (en) | 1978-07-04 |
| IT1104135B (en) | 1985-10-14 |
| NL7800209A (en) | 1978-07-11 |
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