Acetic Acid → HCID 57287692, compound

HRID 1650312Notes

Reaction equation

HRID 1650312 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([O:12]C(=O)C2C=CC=CC=2)[CH2:9][C@H:8]1[CH:21]=[C:22]([CH3:26])[C:23](=[O:25])[CH3:24])=[O:6])[CH:2]=[CH2:3].C[O-].[Na+].C(O)(=O)C.C(OCC)(=O)C>CO.[Cl-].[Na+].O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([OH:12])[CH2:9][C@H:8]1[CH:21]=[C:22]([CH3:26])[C:23](=[O:25])[CH3:24])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 57265826HCID 57265826, compound

Product 1

HCID 57287692HCID 57287692, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (2S,4S)-1-allyloxycarbonyl-4-benzoyloxy-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (0.23 g) in methanol (5 ml) was added 28% solution of sodium methoxide in methanol (0.13 ml) at ° C. and the resulting mixture was stirred at the same temperature for 1 hour. To this solution was added acetic acid (0.04 ml), and the mixture was poured into a mixture of brine and ethyl acetate. The organic layer was separated, washed three times with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (20 ml) eluting with a mixture of n-hexane and ethyl acetate (1:1 V/V) to give (2S,4S)-1-allyloxycarbonyl- 4-hydroxy-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (0.14 g).

Workup

  1. customThe organic layer was separated
  2. washwashed three times with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (20 ml)
  6. washeluting with a mixture of n-hexane and ethyl acetate (1:1 V/V)

Sources & evidence

ORD record
ord-688793129d4d42f39e2e8d822feee2ec
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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