Dichloromethane → HCID 70606043, compound

HRID 2163287Notes

Reaction equation

HRID 2163287 reaction equation
ClCCl.[C:4]([O:8][C:9]([C:11]([N:16]1[CH:19]([S:20]C=O)[CH:18]([NH:23][C:24](=[O:33])[CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:17]1=[O:34])=[C:12]([OH:15])[CH2:13]Br)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(O)(=O)C>[O:26]([CH2:25][C:24]([NH:23][CH:18]1[C:17](=[O:34])[N:16]2[C:11]([C:9]([O:8][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:10])=[C:12]([OH:15])[CH2:13][S:20][C@H:19]12)=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 76211239HCID 76211239, compound

Product 1

HCID 70606043HCID 70606043, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 391 mg. of mercuric acetate in 15 ml. of dichloromethane containing 15 ml. of acetic acid was added in one portion 435 mg. of 1-(1-tert.-butyloxycarbonyl-2-hydroxy-3-bromo-1-propenyl)-3-phenoxyacetamido-4-formylthio-azetidin-2-one. The reaction mixture was stirred at room temperature for 5 minutes, and then hydrogen sulfide gas was bubbled into the reaction mixture for 1 minute. The reaction mixture was filtered through a filter aid and charcoal. The filtrate was evaporated to dryness under reduced pressure to provide tert.-butyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate.

Workup

  1. customhydrogen sulfide gas was bubbled into the reaction mixture for 1 minute
  2. filtrationThe reaction mixture was filtered through a filter aid and charcoal
  3. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-90bd9efd06384682a6707d42798dc493
Source dataset
uspto-grants-1979_01
Patent number
US04133808

Reaction notes

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