Acetic Acid → HCID 14230824, compound

HRID 1759217Notes

Reaction equation

HRID 1759217 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][C:17](OCC(Cl)(Cl)Cl)=O)[N:14]([CH:25]([N+:36]#[C-])[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:13]1=[O:38])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>CN(C)C=O.C(OCC)(=O)C.[Zn]>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:13](=[O:38])[N:14]2[CH:15]1[S:16][CH:17]=[N:36][CH:25]2[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 54167408HCID 54167408, compound

Product 1

HCID 14230824HCID 14230824, compoundYield 48.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 2-[3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1-azetidinyl]-2-isocyanoacetate (2.20 g.) in N,N-dimethylformamide (15 ml.) was added zinc powder (3.30 mg.) at 0° C., and the mixture was stirred at the same temperature for 10 minutes. Thereto was added dropwise acetic acid (2.0 ml.) over a period of 3 minutes and the mixture was stirred at 0° C. for 25 minutes. The reaction mixture was diluted with ethyl acetate (50 ml.) and filtered through a pad of Celite. To the filtrate was added ethyl acetate (50 ml.) and washed with a mixture of 5 to 6% aqueous solution of sodium bicarbonate (60 ml.) and a saturated aqueous solution of sodium chloride (30 ml.), a dilute aqueous solution of sodium chloride (30 ml.×2), a saturated aqueous solution of sodium chloride (30 ml.), water (50 ml.) and a saturated aqueous solution of sodium chloride successively. Drying and removal of the solvent left an amorphous solid (1.51 g.). Chromatography on silica gel (15 g.) with a mixed solvent of methylene chloride and ethyl acetate (5:1 by volume) as an eluent and crystallization from diethyl ether gave benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]oct-3-ene-2-carboxylate (750 mg.), mp 141.5°-143.0° C.

Workup

  1. stirringthe mixture was stirred at 0° C. for 25 minutes
  2. filtrationfiltered through a pad of Celite
  3. additionTo the filtrate was added ethyl acetate (50 ml.)
  4. washwashed with a mixture of 5 to 6% aqueous solution of sodium bicarbonate (60 ml.)
  5. customDrying
  6. customremoval of the solvent
  7. waitleft an amorphous solid (1.51 g.)
  8. customChromatography on silica gel (15 g.) with a mixed solvent of methylene chloride and ethyl acetate (5:1 by volume) as an eluent and crystallization from diethyl ether

Sources & evidence

ORD record
ord-0514b375ce7546b194c0c9581996ad4b
Source dataset
uspto-grants-1982_07
Patent number
US04339449

Reaction notes

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