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

HRID 1804362Notes

Reaction equation

HRID 1804362 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH3:24])[C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].[O:25]=[C:26]1[NH:30][C@H:29]([CH2:31][O:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:28][O:27]1>>[C:33]([O:32][CH2:31][C@@H:29]1[CH2:28][O:27][C:26](=[O:25])[N:30]1[C:20]1[CH:21]=[CH:22][C:17]([C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:6]3[C:5]([CH3:24])=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=3)[CH2:10][CH2:11]2)=[O:16])=[CH:18][CH:19]=1)(=[O:40])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

3

Reactant 2

HCID 16213752(4S)-4-(Benzoyloxymethyl)oxazolidine-2-oneHCID 58484605[4-(5-Ethyl-3-methylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone

Product 1

HCID 58484782(R)-4-benzoyloxymethyl-3-{4-[4-(5-ethyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-oneYield 95.6%

Procedure

By reaction and treatment in the same manner as in Preparation Example 91 and using [4-(5-ethyl-3-methylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone (2.18 g) described in Preparation Example 177 and benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (1.11 g), the title compound (2.53 g) was obtained.

Workup

  1. customBy reaction and treatment in the same manner
  2. customas in Preparation Example 91

Sources & evidence

ORD record
ord-9c1f11bbc358459ea0d0b9e22bbed94e
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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