(4S)-4-(Benzoyloxymethyl)oxazolidine-2-one → (R)-4-hydroxymethyl-3-{5-[4-(3,5,6-trimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}oxazolidin-2-one

HRID 1804326Notes

Reaction equation

HRID 1804326 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]([CH3:23])=[C:18]([CH3:24])[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>>[OH:32][CH2:31][C@@H:29]1[CH2:28][O:27][C:26](=[O:25])[N:30]1[C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[C:18]([CH3:24])[N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 16213752(4S)-4-(Benzoyloxymethyl)oxazolidine-2-oneHCID 58484612(6-Bromopyridin-3-yl)[4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484619(R)-4-hydroxymethyl-3-{5-[4-(3,5,6-trimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}oxazolidin-2-oneYield 50%

Procedure

By reaction and treatment in the same manner as in Example 19 and using (6-bromopyridin-3-yl)[4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone (540 mg) described in Preparation Example 146 and benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (474 mg), the title compound (295 mg) was obtained.

Workup

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

Sources & evidence

ORD record
ord-133ebbc2403b415e97c03e3141c30d5f
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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