Trichloroisocyanuric Acid → (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732381ノート

反応式

HRID 732381 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]1[C@H:14]1[O:18][C:17]([CH3:20])([CH3:19])[N:16]([C:21](=[O:23])[CH3:22])[C@H:15]1[CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.CC1(C)N([O])C(C)(C)CCC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[O:13])[CH2:10][C@@H:9]1[C@H:14]1[O:18][C:17]([CH3:19])([CH3:20])[N:16]([C:21](=[O:23])[CH3:22])[C@H:15]1[CH2:24][C:25]1[CH:26]=[C:27]([F:32])[CH:28]=[C:29]([F:31])[CH:30]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 68814386(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 68814480(R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester収率 100.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Cool to 0° C. a solution of (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.01 gr, 0.022 mmol) in dichloromethane (0.5 mL). Add trichloroisocyanuric acid (0.023 g, 0.110 mmol). Stir 5 minutes and then add TEMPO (2,2,6,6-tetramethyl-1-piperidinyl-oxy, free radical, 0.0007 g, 0.0044 mmol). After one hour add dichloromethane to the mixture and wash with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride. Dry over magnesium sulfate and concentrate under reduced pressure to provide the desired compound (0.010 g, 95%).

後処理

  1. washwash with saturated aqueous sodium bicarbonate
  2. dry with materialDry over magnesium sulfate
  3. concentrationconcentrate under reduced pressure

出典と根拠

ORDレコード
ord-767cbb593110495cb8896e6e4f5553a6
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

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