Potassium borohydride → HCID 13892058, compound

HRID 1903573Notes

Reaction equation

HRID 1903573 reaction equation
[BH4-].[K+].[CH:3]([O:16][C:17]([C:19]1[N:24]2[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:23]2[S:22][CH2:21][C:20]=1N1CCCC1)=[O:18])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CN(C)C=O.C(Cl)Cl.C(O)C.C(O)(=O)C>[CH:3]([O:16][C:17]([C:19]1[N:24]2[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:23]2[S:22][CH2:21][CH:20]=1)=[O:18])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 2

HCID 4192641Potassium borohydrideHCID 70454231HCID 70454231, compound

Product 1

HCID 13892058HCID 13892058, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

While cooling with ice, a solution of 5.4 g (100 mmols) of potassium borohydride in 50 ml of dimethyl formamide is added over 1 hour to a solution of 11.4 g (20 mmols) of 7β-phenoxyacetylamino-3-pyrrolidino-3-cephem-4-carboxylic acid benzhydryl ester in 50 ml of methylene chloride, 50 ml of ethanol and 50 ml of glacial acetic acid. The mixture is then stirred for 36 hours at room temperature, concentrated to half its volume, diluted with ice-water, and extracted several times with methylene chloride. The solvent is then removed by vacuum distillation, affording 7β-phenoxyacetylamino-3-cephem-4-carboxylic acid benzhydryl ester as a white foam.

Workup

  1. temperatureWhile cooling with ice
  2. concentrationconcentrated to half its volume
  3. additiondiluted with ice-water
  4. extractionextracted several times with methylene chloride
  5. customThe solvent is then removed by vacuum distillation

Sources & evidence

ORD record
ord-706c4a50858140c599b34ba9a6fefacc
Source dataset
uspto-grants-1984_03
Patent number
US04436903

Reaction notes

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