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

HRID 1719342Notes

Reaction equation

HRID 1719342 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d99d9711469648e1bfd909b0bf4394e9
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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