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EP0430096A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Process for the production of 3,4-epoxybutyrate and intermediate therefor

Assignee: Kanegafuchi Chemical Industry Co Ltd
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Filing: 1990-11-23
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Granted: —
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Expires: 2010-11-23
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Abstract

Abstract A 3,4-epoxybutyrate of the formula: wherein R 1 is an alkyl or aralkyl group is efficiently prepared by a process comprising steps of: (a) reacting 3,4-dihydroxybutyronitrile of the formula: with a sulfonyl chloride of the formula: R 2 -SO 2 -CI wherein R 2 is an alkyl group or a phenyl group which may be substituted in the presence of a base to obtain a compound of the formula: (b) reacting the compound prepared in the step (a) with an alcohol of the formula: R 1 -OH in the presence of an acid to obtain a compound of the formula: and (c) reacting the compound prepared in the step (b) with a base to obtain the 3,4-epoxybutyrate.

Inventors

  • 👤 Naoaki Taoka
  • 👤 Kenji Inoue
  • 👤 Shigeo Hayashi
  • 👤 Noboru Ueyama
  • 👤 Satomi Takahashi

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-03 17:54
CPC Classifications
C; C07; C07C; C07C309/00; C07C309/01; C07C309/28; C07C309/57; C07C309/58; C07D; C07D303/00; C07D303/02; C07D303/38; C07D303/40; C07C309/63; C07C309/64; C07C309/65; C07C309/72; C07C309/73

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 142 words
A process for the production of a 3, 4-epoxybutyrate of the formula: wherein R' is an alkyl or aralkyl group, which comprises steps of: (a) reacting 3,4-dihydroxybutyronitrile of the formula: with a sulfonyl chloride of the formula: wherein R 2 is an alkyl group or a phenyl group which may be substituted in the presence of a base to obtain a compound of the formula: wherein R 2 is the same as defined above, (b) reacting the compound (IV) obtained in the step (a) with an alcohol of the formula: wherein R 1 is the same as defined above in the presence of an acid to obtain a compound of the formula: wherein R 1 and R 2 are the same as defined above, and (c) reacting the compound (VI) with a base to cyclize the compound (VI) to obtain the 3,4-epoxybutyrate.
Claim 2
Dependent Claim 142 words
A process for the production of a 3, 4-epoxybutyrate of the formula: wherein R' is an alkyl or aralkyl group, which comprises steps of: (a) reacting 3,4-dihydroxybutyronitrile of the formula: with a sulfonyl chloride of the formula: wherein R 2 is an alkyl group or a phenyl group which may be substituted in the presence of a base to obtain a compound of the formula: wherein R 2 is the same as defined above, (b) reacting the compound (IV) obtained in the step (a) with an alcohol of the formula: wherein R 1 is the same as defined above in the presence of an acid to obtain a compound of the formula: wherein R 1 and R 2 are the same as defined above, and (c) reacting the compound (VI) with a base to cyclize the compound (VI) to obtain the 3,4-epoxybutyrate.
Claim 3
Dependent Claim 20 words
The process according to claim 1, wherein optically active (3S)-3,4-dihydroxybutyronitrile is used as the compound (II), and (3S)-3,4-epoxybutyrate is prepared.
Claim 4
Dependent Claim 20 words
The process according to claim 1, wherein optically active (3R)-3,4-dihydroxybutyronitrile is used as the compound (II), and (3R)-3,4-epoxybutyrate is prepared.
Claim 5
Dependent Claim 31 words
A 3,4-dihydroxybutyric acid derivative of the formula: wherein R 1 is an alkyl or aralkyl group and R 2 is an alkyl group or a phenyl group which may be substituted.
Claim 6
Dependent Claim 31 words
A 3,4-dihydroxybutyric acid derivative of the formula: wherein R 1 is an alkyl or aralkyl group and R 2 is an alkyl group or a phenyl group which may be substituted.
Claim 7
Dependent Claim 30 words
The 3,4-dihydroxybutyric acid derivative according to claim 1, which is a compound of the formula: wherein R 1 and R 2 are the same as defined above having the (3S)-configuration.
Claim 8
Dependent Claim 30 words
The 3,4-dihydroxybutyric acid derivative according to claim 1, which is a compound of the formula: wherein R 1 and R 2 are the same as defined above having the (3R)-configuration.

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