(R)-4-Methyloxazolidin-2-one → (R)-3-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]-3-(1,1-dioxoisothiazolidin-2-yl)phenyl}-4-methyloxazolidin-2-one

HRID 1804379Notes

Reaction equation

HRID 1804379 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[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[CH2:12][CH2:11]2)=[O:9])=[C:4]([N:24]2[CH2:28][CH2:27][CH2:26][S:25]2(=[O:30])=[O:29])[CH:3]=1.[CH3:31][C@@H:32]1[CH2:36][O:35][C:34](=[O:37])[NH:33]1>>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:33]3[C@H:32]([CH3:31])[CH2:36][O:35][C:34]3=[O:37])=[CH:3][C:4]=2[N:24]2[CH2:28][CH2:27][CH2:26][S:25]2(=[O:30])=[O:29])=[O:9])[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 58484743[4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

Product 1

HCID 58484815(R)-3-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]-3-(1,1-dioxoisothiazolidin-2-yl)phenyl}-4-methyloxazolidin-2-oneYield 87.5%

Procedure

By reaction and treatment in the same manner as in Example 149 and using [4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (492 mg) described in Preparation Example 181 and (R)-4-methyloxazolidin-2-one (121 mg) described in Preparation Example 25, the title compound (448 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 149
  2. customdescribed in Preparation Example 25

Sources & evidence

ORD record
ord-245718516c75474a95f7aee572171155
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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