Acetic Acid → HCID 86735872, compound

HRID 867232Notes

Reaction equation

HRID 867232 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:16](=[O:17])[N:15]2[C@@H:10]1[CH2:11][S:12][CH:13]=[C:14]2[C:18]([O:20]CC(Cl)(Cl)Cl)=[O:19])=[O:7])([CH3:4])(C)C.Cl.[C:27](O)(=O)[CH3:28]>CN(C)C=O.O.[Zn]>[CH2:1]([O:5][C:6]([NH:8][C@H:9]1[C:16](=[O:17])[N:15]2[C@@H:10]1[CH2:11][S:12][CH:13]=[C:14]2[C:18]([OH:20])=[O:19])=[O:7])[CH2:4][CH2:27][CH3:28]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 86735450HCID 86735450, compound

Product 1

HCID 86735872HCID 86735872, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 43 mg (0.1 mmole) of trichloroethyl cis-7-t-butoxycarbonylamino-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate in 6 ml of dimethylformamide and 6 ml of acetic acid is added over a 1.5 hr period 250 mg (3.8 mmole) zinc dust. The mixture is stirred vigorously for 3 hrs and then diluted with 50 ml of water. The mixture is acidified with dilute HCl, filtered and extracted with ethyl acetate. The organic phase is extracted with 5% NaHCO3 which is acidified and reextracted into ethyl acetate. The final extracts are washed with brine, dried, and evaporated to give cis-7-butoxycarbonylamino-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

  1. filtrationfiltered
  2. extractionextracted with ethyl acetate
  3. extractionThe organic phase is extracted with 5% NaHCO3 which
  4. washThe final extracts are washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-7a1c92acc97f411b90b405070d209763
Source dataset
uspto-grants-1978_07
Patent number
US04103086

Reaction notes

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