Acetic Acid → HCID 56636482, compound

HRID 851360Notes

Reaction equation

HRID 851360 reaction equation
C([O:3][CH:4]([C@@H:6]1[C@@H:9]([S:10][CH3:11])[N:8]([C:12](=[C:17]([CH3:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14])[C:7]1=[O:20])[CH3:5])=O.C[O-].[Na+].C(O)(=O)C>CO>[OH:3][CH:4]([C@@H:6]1[C@@H:9]([S:10][CH3:11])[N:8]([C:12](=[C:17]([CH3:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14])[C:7]1=[O:20])[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 56623594HCID 56623594, compound

Product 1

HCID 56636482HCID 56636482, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of a mixture (5:1) of methyl 2-[(3S,4R)-3-{(1RS)-1-formyloxyethyl}-4-methylthio-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (880 mg) in methanol (20 ml) was added a 4.9 M solution of sodium methoxide in methanol (0.60 ml) at 0° C. After 30 minutes, acetic acid (0.20 ml) was added and the mixture was evaporated. The residue was taken up into ethyl acetate (30 ml) and washed with a dilute aqueous sodium bicarbonate. Drying over magnesium sulfate and removal of the solvent left an oil, which was chromatographed on silica gel (25 g) eluting with 5-20% acetone in dichloromethane to give a mixture (5:1) of methyl 2-[(3S,4R)-3-{(1RS)-1-hydroxyethyl}-4-methylthio-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (742 mg).

Workup

  1. customthe mixture was evaporated
  2. washwashed with a dilute aqueous sodium bicarbonate
  3. dry with materialDrying over magnesium sulfate and removal of the solvent
  4. waitleft an oil, which
  5. customwas chromatographed on silica gel (25 g)
  6. washeluting with 5-20% acetone in dichloromethane

Sources & evidence

ORD record
ord-19d29b67d45e46d192c3a7dab6b1f163
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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