Sodium borohydride → HCID 13892058, compound

HRID 1903568Notes

Reaction equation

HRID 1903568 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]=1N1CCOCC1)=[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.[BH4-].[Na+]>CN(C)C=O.C(O)(=O)C.O>[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 2

HCID 4311764Sodium borohydrideHCID 44151031N-{2-[(Diphenylmethoxy)carbonyl]-3-(morpholin-4-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl}-2-phenoxyethanimidic acid

Product 1

HCID 13892058HCID 13892058, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5.86 g (10 mmols) of 7β-phenoxyacetylamino-3-morpholino-3-cephem-4-carboxylic acid benzhydryl ester are dissolved in 25 ml of dimethyl formamide and 25 ml of glacial acetic acid. The solution is cooled to 0° C. and then 2.04 g of sodium borohydride are added in 100 mg portions over 1 hour, with vigorous evolution of gas occurring after each addition. The reaction mixture is stirred for further 5 hours at room temperature, then diluted with 300 ml of water and extracted with four 100 ml portions of methylene chloride. After neutralisation with aqueous sodium bicarbonate solution, the organic phase is concentrated in vacuo and the dimethyl formamide is distilled off in a high vacuum. The oily, orange residue is chromatographed on silica gel with toluene/ethyl acetate (96:5), affording pure 7β-phenoxyacetylamino-3-cephem-4-carboxylic acid benzhydryl ester as a white foam.

Workup

  1. additionafter each addition
  2. extractionextracted with four 100 ml portions of methylene chloride
  3. concentrationAfter neutralisation with aqueous sodium bicarbonate solution, the organic phase is concentrated in vacuo
  4. distillationthe dimethyl formamide is distilled off in a high vacuum
  5. customThe oily, orange residue is chromatographed on silica gel with toluene/ethyl acetate (96:5)

Sources & evidence

ORD record
ord-5651dccfd53345ee8f83e2d0f99d63d2
Source dataset
uspto-grants-1984_03
Patent number
US04436903

Reaction notes

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