Thiophenol → HCID 88703428, compound

HRID 1248030Notes

Reaction equation

HRID 1248030 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:33](=[O:34])[N:12]2[C:13]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])=[C:14]([N:17]=[N+]=[N-])[CH2:15][S:16][C@H:11]12)=[O:8].[C:35]1([SH:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCCl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:33](=[O:34])[N:12]2[C:13]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])=[C:14]([NH2:17])[CH:15]([S:41][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 13564037HCID 13564037, compound

Product 1

HCID 88703428HCID 88703428, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 0.675 g. of p-nitrobenzyl 7β-(2-thienylacetamido)-3-azido-3-cephem-4-carboxylate in 33 ml. of 1,2-dichloroethane were added 5 equivalents (0.74 g.) of thiophenol and the solution was heated at the reflux temperature for 90 min. The reaction mixture was evaporated to dryness and the reaction product residue was chromatographed over 8 g. of silica (Merck, toluene) using 500 ml. of toluene vs. 500 ml. of 50% ethyl acetate:toluene. The early fractions (23-26) contained a mixture of starting material and the title compound. The middle fractions (31-36) contained 0.035 g. of the title compound while the later fractions (45-59) contained 0.236 g. of the 3-amino ester.

Workup

  1. temperaturethe solution was heated at the reflux temperature for 90 min
  2. customThe reaction mixture was evaporated to dryness
  3. customthe reaction product residue was chromatographed over 8 g
  4. additiona mixture of starting material

Sources & evidence

ORD record
ord-789993ce512b4de097763c9c97cf5aaa
Source dataset
uspto-grants-1985_06
Patent number
US04521598

Reaction notes

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