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

HRID 1719342노트

반응식

HRID 1719342 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d99d9711469648e1bfd909b0bf4394e9
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539152

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