N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction

Masumi Suzuki; Takahiro Yamazaki; Hiromichi Ohta; Kyoko Shima; Katsuhide Ohi; Shigeru Nishiyama; Takeshi Sugai

doi:10.1055/s-2000-6508

N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction

Masumi Suzuki, Takahiro Yamazaki, Hiromichi Ohta, Kyoko Shima, Katsuhide Ohi, Shigeru Nishiyama, Takeshi Sugai

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

Abstract

Oxazolidinones were effectively prepared from N-carbamylamino alcohols by treatment with nitrous acid, via N-nitroso compound as the intermediate. A new route to (R)-4-benzyloxazolidinone was developed starting from DL- phenylalanine, utilizing D-hydantoinase-catalyzed enantioselective hydrolysis of 5-benzylhydantoin under the dynamic kinetic resolution conditions, and the subsequent reduction to the precursor for the above-mentioned cyclization reaction, by taking advantage of the intermediates bearing an N-carbamylamino functionality.

Original language	English
Pages (from-to)	189-192
Number of pages	4
Journal	Synlett
Issue number	2
DOIs	https://doi.org/10.1055/s-2000-6508
Publication status	Published - 2000 Jan 1

Keywords

Enzymes
Hydrolysis
N-carbamylamino alcohols
N-nitrosourea
Oxazolidinones

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2000-6508

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abstract = "Oxazolidinones were effectively prepared from N-carbamylamino alcohols by treatment with nitrous acid, via N-nitroso compound as the intermediate. A new route to (R)-4-benzyloxazolidinone was developed starting from DL- phenylalanine, utilizing D-hydantoinase-catalyzed enantioselective hydrolysis of 5-benzylhydantoin under the dynamic kinetic resolution conditions, and the subsequent reduction to the precursor for the above-mentioned cyclization reaction, by taking advantage of the intermediates bearing an N-carbamylamino functionality.",

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T1 - N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction

AU - Suzuki, Masumi

AU - Yamazaki, Takahiro

AU - Ohta, Hiromichi

AU - Shima, Kyoko

AU - Ohi, Katsuhide

AU - Nishiyama, Shigeru

AU - Sugai, Takeshi

PY - 2000/1/1

Y1 - 2000/1/1

N2 - Oxazolidinones were effectively prepared from N-carbamylamino alcohols by treatment with nitrous acid, via N-nitroso compound as the intermediate. A new route to (R)-4-benzyloxazolidinone was developed starting from DL- phenylalanine, utilizing D-hydantoinase-catalyzed enantioselective hydrolysis of 5-benzylhydantoin under the dynamic kinetic resolution conditions, and the subsequent reduction to the precursor for the above-mentioned cyclization reaction, by taking advantage of the intermediates bearing an N-carbamylamino functionality.

AB - Oxazolidinones were effectively prepared from N-carbamylamino alcohols by treatment with nitrous acid, via N-nitroso compound as the intermediate. A new route to (R)-4-benzyloxazolidinone was developed starting from DL- phenylalanine, utilizing D-hydantoinase-catalyzed enantioselective hydrolysis of 5-benzylhydantoin under the dynamic kinetic resolution conditions, and the subsequent reduction to the precursor for the above-mentioned cyclization reaction, by taking advantage of the intermediates bearing an N-carbamylamino functionality.

KW - Enzymes

KW - Hydrolysis

KW - N-carbamylamino alcohols

KW - N-nitrosourea

KW - Oxazolidinones

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N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction

Abstract

Keywords

ASJC Scopus subject areas

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