p-Bromobenzenesulfonyl chloride → Diphenylmethyl 7-Phenoxyacetamido-3-[(4-bromophenylsulfonyl)oxy]-3-cephem-4-carboxylate

HRID 5547

Reaction equation

HRID 5547 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:36](=[O:37])[N:14]2[C:15]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:16]([OH:19])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>C(#N)C.[H][H]>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:36](=[O:37])[N:14]2[C:15]([C:20]([O:22][CH:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:21])=[C:16]([O:19][S:47]([C:44]3[CH:45]=[CH:46][C:41]([Br:40])=[CH:42][CH:43]=3)(=[O:49])=[O:48])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 67789034Diphenylmethyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate

Product 1

HCID 88424480Diphenylmethyl 7-Phenoxyacetamido-3-[(4-bromophenylsulfonyl)oxy]-3-cephem-4-carboxylateYield 54.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 178418361HCID 178418361, compoundSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared via a modification of the synthesis described in U.S. Pat. No. 3,985,737. A solution of 0.51 g (0.001 mole) of diphenylmethyl 7-phenoxyacetamido-3 -hydroxy-3-cephem- 4-carboxylate in 5 mL of acetonitrile was cooled to 0° C. under a nitrogen atmosphere. Then 0.030 g (0.001 mole) of sodium hydride (80% in mineral oil) was added resulting in hydrogen evolution. The reaction mixture was stirred at 0° C. for 5 minutes, and 0.229 g (0.009 mole) of 4-bromobenzenesulfonyl chloride was added. The cooling bath was removed, and the reaction mix stirred at room temperature for 19 hours. The reaction mixture was filtered and the filtrate carbon treated. The carbon was removed followed by the solvent to leave a foam residue. The residue was crystallized from 1-propanol to yield 0.398 g (54%) of the title compound.

Workup

  1. customThe title compound was prepared via a modification of the synthesis
  2. customThe cooling bath was removed
  3. additionthe reaction mix
  4. stirringstirred at room temperature for 19 hours
  5. filtrationThe reaction mixture was filtered
  6. additionthe filtrate carbon treated
  7. customThe carbon was removed
  8. customto leave a foam residue
  9. customThe residue was crystallized from 1-propanol

Sources & evidence

ORD record
ord-8261f787d18e44569a78042ee44a9160
Source dataset
uspto-grants-1993_09
Patent number
US05245027

Linked notes

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