Sodium borohydride → HCID 13091200, compound

HRID 1719297Notes

Reaction equation

HRID 1719297 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][C:10]([O:12][CH:13]([C@@H:15]2[C@@H:18]([CH2:19][CH:20]=[O:21])[NH:17][C:16]2=[O:22])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO.C(O)(=O)C>[OH:21][CH2:20][CH2:19][C@H:18]1[NH:17][C:16](=[O:22])[C@@H:15]1[CH:13]([O:12][C:10]([O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:24][CH:23]=1)=[O:11])[CH3:14]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 57221866HCID 57221866, compound

Product 1

HCID 13091200HCID 13091200, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

(3S,4R)-3-[(1RS)-1-(p-Nitrobenzyloxycarbonyloxy)ethyl]-2-oxo-4-(2-oxoethyl)azetidine (8 mg) was dissolved in methanol (0.8 ml) and sodium borohydride (2 mg) was added at 0° C. The mixture was then stirred for 30 minutes at the same temperature and acetic acid (3 drops) was added. The mixture was evaporated and the residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate, and brine, dried over magnesium sulfate and evaporated. The residue was purified by preparative thin layer chromatography (silica gel) developing with benzene: acetone (1:1) to give (3S,4R)-4-(2-hydroxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)-ethyl]-2-oxoazetidine (5 mg).

Workup

  1. additionwas added
  2. customThe mixture was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with aqueous sodium bicarbonate, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by preparative thin layer chromatography (silica gel)

Sources & evidence

ORD record
ord-1133dfa9343e4e22957728c0c24b238c
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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