(4S)-4-(Benzoyloxymethyl)oxazolidine-2-one → (R)-3-{4-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-3-methylphenyl}-4-hydroxymethyloxazolidin-2-one

HRID 1804299Notes

Reaction equation

HRID 1804299 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH:23]4[CH2:25][CH2:24]4)=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([CH3:26])[CH:3]=1.[O:27]=[C:28]1[NH:32][C@H:31]([CH2:33][O:34]C(=O)C2C=CC=CC=2)[CH2:30][O:29]1>>[CH:23]1([C:19]2[CH:20]=[C:21]([CH3:22])[C:16]([N:13]3[CH2:14][CH2:15][N:10]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([N:32]5[C@H:31]([CH2:33][OH:34])[CH2:30][O:29][C:28]5=[O:27])=[CH:3][C:4]=4[CH3:26])=[O:9])[CH2:11][CH2:12]3)=[N:17][CH:18]=2)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 16213752(4S)-4-(Benzoyloxymethyl)oxazolidine-2-oneHCID 58484636(4-Bromo-2-methylphenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484790(R)-3-{4-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-3-methylphenyl}-4-hydroxymethyloxazolidin-2-oneYield 71.6%

Procedure

By reaction and treatment in the same manner as in Example 19 and using (4-bromo-2-methylphenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (347 mg) described in Preparation Example 130 and benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (278 mg), the title compound (270 mg) was obtained.

Workup

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

Sources & evidence

ORD record
ord-d36f807735704f489e683fe064e60f4d
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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