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Hydrochloric Acid → (2R,4S)-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methyl-4-mercaptopyrrolidine

HRID 1941605
ノート
印刷プレビュー

反応式

HRID 1941605 の反応式
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:7]([CH2:17][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[S:19](=[O:22])(=[O:21])[NH2:20])[CH2:6]1)(=O)C.C[O-].[Na+].C1(C)C=CC=CC=1.Cl>ClCCl.CO.O>[C:13]([O:12][C:10]([N:8]1[CH2:9][C@@H:5]([SH:4])[CH2:6][C@@H:7]1[CH2:17][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[S:19](=[O:22])(=[O:21])[NH2:20])=[O:11])([CH3:15])([CH3:16])[CH3:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 10942334Sodium MethoxideHCID 57156698(2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine2 回

生成物 1

HCID 10549579(2R,4S)-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methyl-4-mercaptopyrrolidine

試薬・触媒・溶媒 3

HCID 887Methanol溶媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine (i.e., a substrate) in dichloromethane, 4.92M sodium methoxide (NaOMe) in methanol is added. The mixture is stirred. The conditions for this reaction are shown in Table 3, Step A-7. The reaction mixture is diluted with water. The water layer is taken, toluene is added thereto, and acidified with conc. hydrochloric acid under ice cooling. The organic layer is taken, successively washed with water and saturated brine, dried over magnesium sulfate, and concentrated in vacuo to give (2R,4S)-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methyl-4-mercaptopyrrolidine. mp. 90.0° to 91.5° C.

後処理

  1. washsuccessively washed with water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b70a702b7eb746cc8feb8de3ba3b0592
出典データセット
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05703243

反応ノート

読み込み中…

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