Acetic Acid → 51762-51-7

HRID 1905795Notes

Reaction equation

HRID 1905795 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[OH:36])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C(O)(=O)C.O>CN(C)C=O>[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][CH:18]2[OH:36])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 54721268(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Product 1

HCID 1364457351762-51-7Yield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxy-7beta-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester (1) in dimethylformamide (9.5 parts, dried over Molecular Sieves) at -50° C. under nitrogen is added sodium borohydride (4 equivalents) at -53° to -48° C. over 3 minutes. After 30 minutes at the same temperature, glacial acetic acid (1.4 parts) and then water (10 parts) are added to the mixture gradually, and extracted with ethyl acetate. The extract is washed with 5% aqueous sodium hydrogen carbonate and water, dried over sodium sulfate, and concentrated. The residue is crystallized from a mixture of dichloromethane (4 parts) and n-hexane (1.7 parts) to give 3-hydroxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl ester (2). Yield: 76.3%. mp. 196°-198° C. (decomposition).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with 5% aqueous sodium hydrogen carbonate and water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is crystallized from a mixture of dichloromethane (4 parts) and n-hexane (1.7 parts)

Sources & evidence

ORD record
ord-1ecf83c774844dd3b05b38f156ea281f
Source dataset
uspto-grants-1987_03
Patent number
US04647658

Reaction notes

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