Sodium Hydroxide → (2S, 4S)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine

HRID 5078

反応式

HRID 5078 の反応式
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][SH:10])=[CH:7][CH:6]=1.[C:13]([O:17][C:18]([N:20]1[CH2:24][C@H:23](OS(C)(=O)=O)[CH2:22][C@H:21]1[C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[O:19])([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O>[C:13]([O:17][C:18]([N:20]1[CH2:24][C@@H:23]([S:10][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[CH2:22][C@H:21]1[C:30](=[O:34])[N:31]([CH3:32])[CH3:33])=[O:19])([CH3:16])([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 804074-Methoxy-alpha-toluenethiolHCID 57135520(2S, 4R)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-methanesulfonyloxypyrrolidine

生成物 1

HCID 57063871(2S, 4S)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine収率 31.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

151 mg of sodium hydroxide (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 532 mg of 4-methoxybenzyl mercaptan dissolved in 10 ml of dry dimethylformamide. The mixture was then stirred at room temperature for 30 minutes, after which 1.05 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-methanesulfonyloxypyrrolidine [prepared as described in step (2) above] was added. The reaction mixture was then stirred at room temperature for 30 minutes and then at 40° C. for 6 hours. At the end of this time, it was treated and purified according to the procedure described in Preparation 1-(4), to afford 385 mg of the title compound as an oil.

後処理

  1. stirringThe reaction mixture was then stirred at room temperature for 30 minutes
  2. waitat 40° C. for 6 hours
  3. additionAt the end of this time, it was treated
  4. custompurified
  5. customdescribed in Preparation 1-(4)

出典と根拠

ORDレコード
ord-daab5ee4b89e4b57bb5dd1d29f4fa7c5
出典データセット
uspto-grants-1993_09
特許番号
US05242914

関連ノート

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