Sodium borohydride → methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719342ノート

反応式

HRID 1719342 の反応式
[BH4-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C@@H:14]1[C@@H:17]([CH2:18][CH:19]=[O:20])[N:16]([C:21](=[C:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])[C:15]1=[O:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([O:10][C:11]([NH:13][C@@H:14]1[C@@H:17]([CH2:18][CH2:19][OH:20])[N:16]([C:21](=[C:26]([CH3:27])[CH3:28])[C:22]([O:24][CH3:25])=[O:23])[C:15]1=[O:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 54489122methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-2-oxo-4-(2-oxoethyl)azetidin-1-yl]-3-methylbut-2-enoate

生成物 1

HCID 54247464methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoate収率 79.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium borohydride (10 mg) was added to a solution of methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-2-oxo-4-(2-oxoethyl)azetidin-1-yl]-3-methylbut-2-enoate (49 mg) in methanol (1 ml) at 0° C. The mixture was stirred at the same temperature for 20 minutes and quenched with acetic acid (~0.05 ml). The resulting solution was evaporated in vacuo. The residue was dissolved in dichloromethane and washed with brine containing sodium bicarbonate. The extract was dried over magnesium sulfate, evaporated, and chromatographed on silica gel (1.5 g, eluting with 5-10% acetone in dichloromethane) to give 39 mg of methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoate.

後処理

  1. customquenched with acetic acid (~0.05 ml)
  2. customThe resulting solution was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with brine
  5. additioncontaining sodium bicarbonate
  6. dry with materialThe extract was dried over magnesium sulfate
  7. customevaporated
  8. customchromatographed on silica gel (1.5 g, eluting with 5-10% acetone in dichloromethane)

出典と根拠

ORDレコード
ord-d99d9711469648e1bfd909b0bf4394e9
出典データセット
uspto-grants-1985_09
特許番号
US04539152

反応ノート

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