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

HRID 1804323Notes

Reaction equation

HRID 1804323 reaction equation
Br[C:2]1[N: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])=[CH:4][CH:3]=1.[O:25]=[C:26]1[NH:30][C@H:29]([CH2:31][O:32]C(=O)C2C=CC=CC=2)[CH2:28][O:27]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:4]=[CH:3][C:2]([N:30]4[C@H:29]([CH2:31][OH:32])[CH2:28][O:27][C:26]4=[O:25])=[N:7][CH:6]=3)=[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 58484652(6-Bromopyridin-3-yl)[4-(5-ethyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484774(R)-3-{5-[4-(5-ethyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-4-hydroxymethyloxazolidin-2-oneYield 54.4%

Procedure

By reaction and treatment in the same manner as in Example 19 and using (6-bromopyridin-3-yl)[4-(5-ethyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (530 mg) described in Preparation Example 145 and benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (466 mg), the title compound (315 mg) was obtained.

Workup

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

Sources & evidence

ORD record
ord-9f72e55245944647934385ee83564fe3
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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