(4S)-4-(Benzoyloxymethyl)oxazolidine-2-one → (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-hydroxymethyloxazolidin-2-one

HRID 1804194Notes

Reaction equation

HRID 1804194 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[O:24]=[C:25]1[NH:29][C@H:28]([CH2:30][O:31]C(=O)C2C=CC=CC=2)[CH2:27][O:26]1>>[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:29]4[C@H:28]([CH2:30][OH:31])[CH2:27][O:26][C:25]4=[O:24])=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 2

HCID 16213752(4S)-4-(Benzoyloxymethyl)oxazolidine-2-oneHCID 58484535[4-(3,5-Dimethylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone

Product 1

HCID 67381278(R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-hydroxymethyloxazolidin-2-oneYield 48.9%

Procedure

By reaction and treatment in the same manner as in Example 19 and using [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone (2.1 g) described in Preparation Example 77 and benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (1.3 g), the title compound (1 g) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 19

Sources & evidence

ORD record
ord-78ec6fc3d4f24faeb39e255aa0858a64
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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