Acetic Acid → HCID 13892058, compound

HRID 1903570Notes

Reaction equation

HRID 1903570 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:21]2[S:20][CH2:19][C:18]=1N1CCCCC1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BH4-].[Na+]>CN(C)C=O.O.O.O.O.O.O.[Co](Cl)Cl>[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:21]2[S:20][CH2:19][CH:18]=1)=[O:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 4311764Sodium borohydrideHCID 70504007HCID 70504007, compound

Product 1

HCID 13892058HCID 13892058, compound

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 6228DimethylformamideSolvent

Procedure

4.76 g (20 mmols) of cobalt(II) chloride hexahydrate are added in several portions, at 0°-5° C., to a solution of 11.7 g (20 mmols) of 7β-phenoxyacetylamino-3-piperidino-3-cephem-4-carboxylic acid benzhydryl ester in 50 ml of dimethyl formamide. The solution turns dark blue. Then 75 ml of glacial acetic acid are added dropwise at 0° C. over 30 minutes. Then 4.08 g (120 mmols) of sodium borohydride are added in 200 mg portions over 1 hour, with vigorous evolution of gas after each addition. When the addition is complete, the reaction mixture is warmed to room temperature and, after the addition of a further 50 ml of glacial acetic acid, stirred for 36 hours at room temperature. The dark red solution is filtered to remove the pink precipitate, the filter residue is washed with methylene chloride, and the filtrate is concentrated in vacuo. The dimethyl formamide is distilled off in a high vacuum. The oily residue is dissolved in methylene chloride and washed three times with 50 ml of water. The methylene chloride solution is filtered over 50 g of silica gel to remove residual cobalt salts and the eluate is concentrated, affording pure 7β-phenoxyacetylamino-3-cephem-4-carboxylic acid benzhydryl ester as a white foam.

Workup

  1. additionafter each addition
  2. additionWhen the addition
  3. filtrationThe dark red solution is filtered
  4. customto remove the pink precipitate
  5. washthe filter residue is washed with methylene chloride
  6. concentrationthe filtrate is concentrated in vacuo
  7. distillationThe dimethyl formamide is distilled off in a high vacuum
  8. dissolutionThe oily residue is dissolved in methylene chloride
  9. washwashed three times with 50 ml of water
  10. filtrationThe methylene chloride solution is filtered over 50 g of silica gel
  11. customto remove residual cobalt salts
  12. concentrationthe eluate is concentrated

Sources & evidence

ORD record
ord-2370606fa07e41ce8bc25167aca45242
Source dataset
uspto-grants-1984_03
Patent number
US04436903

Reaction notes

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