(4S)-4-(Benzoyloxymethyl)oxazolidine-2-one → (R)-4-[4-(4-benzoyloxymethyl-2-oxooxazolidin-3-yl)2-fluoro-benzoyl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1804109Notes

Reaction equation

HRID 1804109 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][C:16]=2[F:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:24]=[C:25]1[NH:29][C@H:28]([CH2:30][O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:27][O:26]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([N:29]3[C@H:28]([CH2:30][O:31][C:32](=[O:39])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:27][O:26][C:25]3=[O:24])=[CH:17][C:16]=2[F:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 16213752(4S)-4-(Benzoyloxymethyl)oxazolidine-2-oneHCID 51306443HCID 51306443, compound

Product 1

HCID 54755235(R)-4-[4-(4-benzoyloxymethyl-2-oxooxazolidin-3-yl)2-fluoro-benzoyl]piperazine-1-carboxylic acid tert-butyl esterYield 49.9%

Procedure

By reaction and treatment in the same manner as in Preparation Example 91 and using 4-(4-bromo-2-fluorobenzoyl)piperazine-1-carboxylic acid tert-butyl ester (3.49 g) described in Preparation Example 154 and benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (1.99 g), the title compound (2.37 g) was obtained.

Workup

  1. customBy reaction and treatment in the same manner
  2. customas in Preparation Example 91

Sources & evidence

ORD record
ord-c3888c2eaf074f35bf9f74dbd0b30ad4
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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