Dimethylformamide → p-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-pyrrolidino-3-cephem4-carboxylate

HRID 462265Notes

Reaction equation

HRID 462265 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:14](Cl)[CH2:15][S:16][C@H:11]12)=[O:8].CN(C=O)C.[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>[Cl-].[Na+].O.C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:14]([N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 705589584-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate

Product 1

HCID 70632343p-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-pyrrolidino-3-cephem4-carboxylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 0.988 g. (2 mmole) of p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate in 10 ml. of dry DMF maintained at ice-bath temperature were added 0.375 ml. (4.4 mmole) of pyrrolidine. The reaction mixture was allowed to stir for about one hour and the mixture was then diluted with brine and ethyl acetate. The ethyl acetate was washed with brine several times and dried over magnesium sulfate. Evaporation of the dried extract gave 845 mg. of product.

Workup

  1. additionwere added 0.375 ml
  2. washThe ethyl acetate was washed with brine several times
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the dried
  5. extractionextract
  6. customgave 845 mg

Sources & evidence

ORD record
ord-452613959a274cb5a4a8c7451e558150
Source dataset
uspto-grants-1977_12
Patent number
US04065618

Reaction notes

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