Dichloromethane → HCID 70606043, compound

HRID 436269Notes

Reaction equation

HRID 436269 reaction equation
C(Cl)Cl.[OH:4][C:5](CBr)=[C:6]([N:14]1[C:17](=[O:18])[CH:16]([NH:19][C:20](=[O:29])[CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:15]1[S:30][CH:31]=O)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>C(O)(=O)C>[O:22]([CH2:21][C:20]([NH:19][CH:16]1[C:17](=[O:18])[N:14]2[C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([OH:4])[CH2:31][S:30][C@H:15]12)=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][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 0.391 g. (1.mmol.) of mercuric acetate in a mixture of 15 ml. of methylene chloride and 15 ml. of acetic acid was added, as a neat solid, 0.435 g. (1 mmol.) of t-butyl 3-hydroxy-4-bromo-2-(2-formylthio-4-oxo-3-phenoxyacetamido-1-azetidinyl)-2-butenoate. The resulting mixture was stirred for five minutes at room temperature after which time the solution became cloudy. Hydrogen sulfide was bubbled into the mixture, and the mixture was filtered through a filter aide an charcoal. The filtrate was evaporated to a residue to obtain t-butyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate.

Workup

  1. customHydrogen sulfide was bubbled into the mixture
  2. filtrationthe mixture was filtered through a filter aide an charcoal
  3. customThe filtrate was evaporated to a residue

Sources & evidence

ORD record
ord-8840278411dd4d81955e449f54650893
Source dataset
uspto-grants-1977_02
Patent number
US04008230

Reaction notes

Loading…