Ethyl Acetate → HCID 67915270, compound

HRID 1650303Notes

Reaction equation

HRID 1650303 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16](=[O:37])[CH:17]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[NH:13][C:12]1=[O:38])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:39]([O:42][C:43]([N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[CH:50]=O)=[O:44])[CH:40]=[CH2:41].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:39]([O:42][C:43]([N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1/[CH:50]=[CH:17]/[C:16](=[O:37])[CH2:15][C@H:14]1[NH:13][C:12](=[O:38])[C@@H:11]1[C@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[CH3:10])=[O:44])[CH:40]=[CH2:41]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 53958006HCID 53958006, compoundHCID 57132120HCID 57132120, compound

Product 1

HCID 67915270HCID 67915270, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-(3-triphenylphosphoranylidene-2-oxopropyl)-2-oxoazetidine (572 mg) and (2S)-1-allyloxycarbonyl-2-formylpyrrolidine (201.5 mg) in toluene (5 ml) was heated to reflex for three hours. Evaporation of the solvent gave a residue, which was taken up into ethyl acetate. The resultant precipitate was filtered off and washed with ethyl acetate. The filtrate and the washings were combined and evaporated in vacuo. The residue was chromatographed on silica gel (50 ml) eluting with a mixture of n-hexane and ethyl acetate (2:1-1:1-1:3 V/V) to give (3S,4R)-4-[(E)-4-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-2-oxo-3-butenyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (297.7 mg).

Workup

  1. customEvaporation of the solvent
  2. customgave a residue, which
  3. filtrationThe resultant precipitate was filtered off
  4. washwashed with ethyl acetate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (50 ml)
  7. washeluting with a mixture of n-hexane and ethyl acetate (2:1-1:1-1:3 V/V)

Sources & evidence

ORD record
ord-e2837dd63e5a44919f0b05f321023198
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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