(R)-(+)-4-Isopropyl-5,5-dimethyl-2-oxazolidinone → (R)-3-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one

HRID 1804157Notes

Reaction equation

HRID 1804157 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]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:3]=1.[CH:28]([C@@H:31]1[C:35]([CH3:37])([CH3:36])[O:34][C:33](=[O:38])[NH:32]1)([CH3:30])[CH3:29]>>[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:32]3[C@H:31]([CH:28]([CH3:29])[CH3:30])[C:35]([CH3:36])([CH3:37])[O:34][C:33]3=[O:38])=[CH:3][C:4]=2[S:24]([CH3:27])(=[O:26])=[O:25])=[O:9])[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 10583042(R)-(+)-4-Isopropyl-5,5-dimethyl-2-oxazolidinoneHCID 58484856(4-Bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

Product 1

HCID 67381018(R)-3-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}-4-isopropyl-5,5-dimethyloxazolidin-2-oneYield 42.8%

Procedure

By reaction and treatment in the same manner as in Example 1 and using (4-bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (722 mg) described in Preparation Example 9 and (R)-(+)-4-isopropyl-5,5-dimethyloxazolidin-2-one (250 mg), the title compound (359 mg) was obtained.

Workup

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

Sources & evidence

ORD record
ord-a40b65cab9194b8d96f43164398b4cd1
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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