Dimethyl Sulfoxide → HCID 68132076, compound

HRID 1605403Notes

Reaction equation

HRID 1605403 reaction equation
BrC[CH2:3][C:4]1[CH2:5][S:6](=[O:31])[C@@H:7]2[CH:19]([NH:20][C:21](=[O:29])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18](=[O:30])[N:8]2[C:9]=1[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11].CS(C)=[O:34].O>C1C=CC=CC=1.CS(C)=O>[OH:34][CH2:3][C:4]1[CH2:5][S:6](=[O:31])[C@@H:7]2[CH:19]([NH:20][C:21](=[O:29])[CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:18](=[O:30])[N:8]2[C:9]=1[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:15])[Cl:16])=[O:11]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 962Water2×HCID 131710135HCID 131710135, compound

Product 1

HCID 68132076HCID 68132076, compound

Reagents, catalysts & solvents 1

HCID 18518713Benzene dimethylsulfoxideSolvent

Procedure

To a solution of 0.461 (0.82 mmole) of 2,2,2-trichloroethyl 3-bromoethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide in 20 ml of 1:1 benzene-dimethylsulfoxide (DMSO) is added 0.150 ml (8.2 mmoles) of water and the mixture is stirred at 25° for 7 days. Then the mixture is poured into 100 ml of H2O and extracted with ethyl acetate. The ethyl acetate is dried (MgSO4) and evaporated in vacuo to yield 2,2,2-trichloroethyl 3-hydroxymethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide, which can be purified by recrystallization from methanol.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate is dried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-fc80919241ae4291ab17324aeb89baa7
Source dataset
uspto-grants-1976_04
Patent number
US03950329

Reaction notes

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