Thioacetic acid → HCID 54394538、化合物

HRID 620775

反応式

HRID 620775 の反応式
CS(O[C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([CH2:24][O:25][CH2:26][CH2:27][NH:28][C:29]([NH2:31])=[O:30])[CH2:7]1)(=O)=O.[C:32]([SH:35])(=[O:34])[CH3:33].[H-].[Na+]>CN(C)C=O>[C:32]([S:35][C@@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([CH2:24][O:25][CH2:26][CH2:27][NH:28][C:29]([NH2:31])=[O:30])[CH2:7]1)(=[O:34])[CH3:33]

参加物

5

反応物 3

HCID 10484Thioacetic acidHCID 24758Sodium hydrideHCID 54429997HCID 54429997、化合物

生成物 1

HCID 54394538HCID 54394538、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (1.37 g) in dimethylformamide (3 ml) was added to a reaction mixture of thioacetic S-acid (0.32 ml) and sodium hydride (62.8% in oil suspension) (0.14 g) in dimethylformamide (7 ml) in a nitrogen stream, and the mixture was heated at 70°-75° C. for 5 hours. The reaction mixture was poured into ice-water (100 ml), extracted with ethyl, acetate (50 ml×2), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (20 g) and eluted with a mixture of methanol and chloroform (2:98 V/V) to give (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (1.02 g).

後処理

  1. temperaturethe mixture was heated at 70°-75° C. for 5 hours
  2. extractionextracted with ethyl, acetate (50 ml×2)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a syrup
  6. washeluted with a mixture of methanol and chloroform (2:98 V/V)

出典と根拠

ORDレコード
ord-bf0bdcfcfcce4ccc93bbafee1d42e0a0
出典データセット
uspto-grants-1989_04
特許番号
US04822787

関連ノート

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