Hydrochloric Acid → (2S,4S)-allyl 2-(((allyloxycarbonyl)(sulfamoyl)amino)methyl)-4-mercaptopyrrolidine-1-carboxylate

HRID 1034531ノート

反応式

HRID 1034531 の反応式
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@H:7]([CH2:16][N:17]([S:24](=[O:27])(=[O:26])[NH2:25])[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[CH2:6]1)(=O)C.C[O-].[Na+].CO.Cl>C1(C)C=CC=CC=1.O>[CH2:13]([O:12][C:10]([N:8]1[CH2:9][C@@H:5]([SH:4])[CH2:6][C@H:7]1[CH2:16][N:17]([S:24](=[O:26])(=[O:27])[NH2:25])[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])=[O:11])[CH:14]=[CH2:15]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 57143963(2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(N-sulfamoyl-N-allyloxycarbonylamino)methylpyrrolidine

生成物 1

HCID 57114535(2S,4S)-allyl 2-(((allyloxycarbonyl)(sulfamoyl)amino)methyl)-4-mercaptopyrrolidine-1-carboxylate収率 78.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

To a solution of (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(N-sulfamoyl-N-allyloxycarbonylamino)methylpyrrolidine (6.70 g: 16.4 mmole) in toluene (50 ml), 4.92M solution of sodium methoxide in methanol (5.0 ml: 24.7 mmole) is added at -30° C. The mixture is stirred for 30 minutes, and diluted with water (55 ml). The aqueous layer is taken, diluted with toluene (50 ml), acidified with concentrated hydrochloric acid (2.3 ml) under ice cooling, and stirred. The organic layer is taken, successively washed with water and saturated brine, dried over magnesium sulfate and concentrated in vacuo. The residual oil is purified by silica gel chromatography (toluene-ethyl acetate) to give (2S,4S)-1-allyloxycarbonyl-2-(N-sulfamoyl-N-allyloxycarbonylamino)methyl-4-mercaptopyrrolidine (4.89 g). Yield: 78%. Colorless oil. NMR δ(CDCl3) ppm: 1.5 to 1.7(m, 1H), 2.35(s, 3H), 2.5 to 2.7(m, 1H), 3.19(dd, J=6.3 Hz, J=11.5 Hz, 1H), 3.68(dd, J=3.8 Hz, J=14.5 Hz, 1H), 3.9 to 4.3(m, 3H), 4.3 to 4.7(m, 5H), 5.2 to 5.4(m, 4H), 5.8 to 6.1(m, 4H). IR ν (CHCl3) cm-1 : 1718, 1684, 1179, 1160.

後処理

  1. stirringstirred
  2. washsuccessively washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residual oil is purified by silica gel chromatography (toluene-ethyl acetate)

出典と根拠

ORDレコード
ord-b5da3e9b07a6484d9a33b326840d4615
出典データセット
uspto-grants-1994_05
特許番号
US05317016

反応ノート

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