Claims
- 1. A process for producing an active ester of an amino acid having a protected amino group which comprises reacting the carboxyl group of an amino acid of the formula, ##STR19## having a protected amino group, wherein R.sup.5 is alkylene or alkylidene having 1-30 carbon atoms which may have a substituent selected from the group consisting of phenyl, salicyl, canbamoyl and carboxyl cycloalkylene or cycloalkylidene having 3-8 carbon atoms, phenylene, a group of the formula ##STR20## a group of the formula ##STR21## or a group in which two or more groups selected from the group consisting of the above-mentioned aliphatic and aromatic hydrocarbon groups are bonded through --CONH--; and R.sup.6 is hydrogen or alkyl having 1-4 carbon atoms, with a phosphonium salt obtained by reacting a phosphorous ester selected from the group consisting of monomethyl, monoethyl, monoisopropyl, monophenyl, dimethyl, diethyl, diisopropyl, di-n-butyl, diphenyl, triethyl, triisopropyl and tributyl esters of phosphorous acid and an ammonium salt of the phosphorous monoester, with an organic base selected from the group consisting of pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,6-dimethylpyridine or triethylamine, and an oxidizing agent selected from the group consisting of bromine, iodine, mercurous chloride, mercuric chloride, mercuric bromide or mercuric acetate, at a temperature of from 30.degree. to 200.degree. C., and then reacting the activated amino acid with a hydroxyl or mercapto group-containing compound of the formula
- R.sup.4 OH (III-a)
- or
- R.sup.4 SH (III-b)
- wherein R.sup.4 is alkyl having 1-18 carbon atoms, cycloalkyl having 3-8 carbon atoms, phenyl, naphthyl, aryl having at least one substituent selected from the group consisting of alkyl having 1-4 carbon atoms, nitro, cyano, N,N-dimethylamino and methoxycarbonyl, or phenylalkyl having 7-12 carbon atoms, at a temperature of from 0.degree. to 200.degree. C.
- 2. A process according to claim 1, wherein the organic base is pyridine.
- 3. A process for producing an active ester of an amino acid having a protected amino group which comprises reacting the hydroxyl or mercapto group of a hydroxyl or mercapto group-containing compound of the formula
- R.sup.4 OH (III-a)
- or
- R.sup.4 SH (III-b)
- wherein R.sup.4 is alkyl having 1-18 carbon atoms, cycloalkyl having 3-8 carbon atoms, phenyl, naphthyl, aryl having at least one substituent selected from the group consisting of alkyl having 1-4 carbon atoms, nitro, cyano, N,N-dimethylamino and methoxycarbonyl, or phenylalkyl having 7-12 carbon atoms, with a phosphonium salt obtained by reacting a phosphorus ester selected from the group consisting of monomethyl, monoethyl, monoisopropyl, monophenyl, dimethyl, diethyl, diisopropyl, di-n-butyl, diphenyl, triethyl, triisopropyl and tributyl esters of phosphorous acid, and an ammonium salt of the phosphorous monoester, with an organic base selected from the group consisting of pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,6-dimethylpyridine or triethylamine, and an oxidizing agent selected from the group consisting of bromine, iodine, mercurous chloride, mercuric chloride, mercuric bromide or mercuric acetate, at a temperature of from 30.degree. to 200.degree. C., and then reacting the activated hydroxyl or mercapto group-containing compound with an amino acid of the formula ##STR22## having a protected amino group, wherein R.sup.5 is alkylene or alkylidene having 1-30 carbon atoms which may have a substituent selected from the group consisting of phenyl, salicyl, carbamoyl and carboxyl cycloalkylene or cycloalkylidene having 3-8 carbon atoms, phenylene, a group of the formula ##STR23## a group of the formula ##STR24## or a group in which two or more groups selected from the group consisting of the above-mentioned aliphatic and aromatic hydrocarbon groups are bonded through --CONH--; and R.sup.6 is hydrogen or alkyl having 1-4 carbon atoms at a temperature of from 0.degree. to 200.degree. C.
- 4. A process according to claim 3, wherein the organic base is pyridine.
Priority Claims (2)
Number |
Date |
Country |
Kind |
46-93872 |
Nov 1971 |
JPX |
|
47-17355 |
Feb 1972 |
JPX |
|
CROSS REFERENCE TO THE RELATED APPLICATION
This is a Division of application Ser. No. 688,289 filed May 20, 1976 which in turn is a division of application Ser. No. 475,877, filed June 3, 1974, now U.S. Pat. No. 3,974,219, which in turn is a continuation-in-part of application Ser. No. 305,256, filed Nov. 10, 1972, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
2938915 |
Schwyzer et al. |
May 1960 |
|
3907855 |
Yamazak et al. |
Sep 1975 |
|
Non-Patent Literature Citations (1)
Entry |
Gawne, G., et al., J. Amer. Chem. Soc. 1969, 91(20), 5669-5671. |
Divisions (2)
|
Number |
Date |
Country |
Parent |
688289 |
May 1976 |
|
Parent |
475877 |
Jun 1974 |
|
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
305256 |
Nov 1972 |
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