Method for producing α-amino acid including phosphorus and production intermediates thereof
AssigneeMeiji Seika Kaisha, Ltd.
InventorsNobuto Minowa, Nozomu Nakanishi, Masaaki Mitomi
Life of this patent
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Abstract
A method for efficiently producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid, useful as a herbicide, by a catalytic asymmetric synthesis reaction with a high asymmetric yield. The method includes a step in which a compound represented by the below formula (1) and a benzylamine are reacted in the presence of dehydrating agent, then the resulting mass is reacted with hydrogen cyanide in the presence of an asymmetric catalyst, followed by acid hydrolysis, further followed by elimination of a protective group. [chemical formula 1] (1) (where, R1 represents a C1-4 alkyl group).
Claims11
A method for producing a compound represented by the following formula (4), wherein a compound represented by the following formula (3) is reacted with hydrogen cyanide under the presence of an asymmetric catalyst:
- [In the formula, R1 represents C1-4 alkyl group, allyl group, C1-4 alkyloxy C1-4 alkyl group, C1-4 alkyloxy C1-4 alkyloxy C1-4 alkyl group, aryl group, substituted aryl group, arylmethyl group, substituted arylmethyl group, tri C1-4 alkylsilyl group or diphenylmethylsilyl group;
- R2 represents allyl group, aryl group, substituted aryl group, arylmethyl group or substituted arylmethyl group];
- [In the formula, R1 and R2 represent the same meaning as aforementioned].
A method for producing a compound represented by the following formula (3), wherein a compound represented by the following formula (1) and a compound represented by the following formula (2) are reacted under the presence of dehydrating agent:
- [In the formula, R1 represents C1-4 alkyl group, allyl group, C1-4 alkyloxy C1-4 alkyl group, C1-4 alkyloxy C1-4 alkyloxy C1-4 alkyl group, aryl group, substituted aryl group, arylmethyl group, substituted arylmethyl group, tri C1-4 alkylsilyl group or diphenylmethylsilyl group];
- R2—NH2 (2)
- [In the formula, R2 represents allyl group, aryl group, substituted aryl group, arylmethyl group or substituted arylmethyl group];
- and
- [In the formula, R1 and R2 represent the same meaning as aforementioned].
A method for producing L-2-amino-4-(hydroxymethylphosphinyl )-butanoic acid represented by the following formula (5);
- said method comprising:
- a process of allowing a compound represented by the following formula (1) to react with a compound represented by the following formula (2) under the presence of dehydrating agent to obtain a compound represented by the following formula (3);
- a process of allowing a compound represented by the following formula (3) to react with hydrogen cyanide under the presence of an asymmetric catalyst to obtain a compound represented by the following formula (4);
- and
- a process of allowing nitrile group in the compound of formula (4) to acid hydrolysis, and further deprotecting hydroxyl group and amino group moieties in the compound of formula (4);
- [In the formula, R1 represents C1-4 alkyl group, allyl group, C1-4 alkyloxy C1-4 alkyl group, C1-4 alkyloxy C1-4 alkyloxy C1-4 alkyl group, aryl group, substituted aryl group, arylmethyl group, substituted arylmethyl group, tri C1-4 alkylsilyl group or diphenylmethylsilyl group];
- R2—NH2 (2)
- [In the formula, R2 represents ally group, aryl group, substituted aryl group, arylmethyl group or substituted arylmethyl group];
- [In the formula, R1 and R2 represent the same meaning as aforementioned];
- and
- [In the formula, R1 and R2 represent the same meaning as aforementioned].
A compound represented by the following formula (3):
- [In the formula, R1 represents C1-4 alkyl group, allyl group, C1-4 alkyloxy C1-4 alkyl group, C1-4 alkyloxy C1-4 alkyloxy C1-4 alkyl group, aryl group, substituted aryl group, arylmethyl group, substituted arylmethyl group, tri C1-4 alkylsilyl group or diphenylmethylsilyl group;
- R2 represents allyl group, aryl group, substituted aryl group, arylmethyl group or substituted arylmethyl group].
A compound represented by the following formula (4):
- [In the formula, R1 represents C1-4 alkyl group, allyl group, C1-4 alkyloxy C1-4 alkyl group, C1-4 alkyloxy C1-4 alkyloxy C1-4 alkyl group, aryl group, substituted aryl group, arylmethyl group, substituted arylmethyl group, tri C1-4 alkylsilyl group or diphenylmethylsilyl group;
- R2 represents allyl group, aryl group, substituted aryl group, arylmethyl group or substituted arylmethyl group].
Dependencies are inferred from the claim text.