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

HRID 1804298Notes

Reaction equation

HRID 1804298 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]([CH2:23][CH3:24])=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([CH3:25])[CH:3]=1.[O:26]=[C:27]1[NH:31][C@H:30]([CH2:32][O:33]C(=O)C2C=CC=CC=2)[CH2:29][O:28]1>>[CH2:23]([C:19]1[CH:20]=[C:21]([CH3:22])[C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:31]4[C@H:30]([CH2:32][OH:33])[CH2:29][O:28][C:27]4=[O:26])=[CH:3][C:4]=3[CH3:25])=[O:9])[CH2:11][CH2:12]2)=[N:17][CH:18]=1)[CH3:24]

Participants

3

Reactant 2

HCID 16213752(4S)-4-(Benzoyloxymethyl)oxazolidine-2-oneHCID 58484569(4-Bromo-2-methylphenyl)[4-(5-ethyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484830(R)-3-{4-[4-(5-ethyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-3-methylphenyl}-4-hydroxymethyloxazolidin-2-oneYield 73.4%

Procedure

By reaction and treatment in the same manner as in Example 19 and using (4-bromo-2-methylphenyl)[4-(5-ethyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (350 mg) described in Preparation Example 129 and benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (289 mg), the title compound (280 mg) was obtained.

Workup

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

Sources & evidence

ORD record
ord-fde82f45abe5430aaea46dd9effc5e15
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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