Hydrochloric Acid → 3-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl ester

HRID 1155333Notes

Reaction equation

HRID 1155333 reaction equation
[BH4-].[Na+].[C:3]1([CH:9]([O:16][C:17]([C:19]2[N:24]3[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:23]3[S:22][CH2:21][C:20]=2[OH:39])=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CN(C)C=O.C(O)(=O)C>[C:3]1([CH:9]([O:16][C:17]([C@@H:19]2[N:24]3[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:23]3[S:22][CH2:21][CH:20]2[OH:39])=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 547082513-Hydroxy-7beta-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

Product 1

HCID 705700963-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

1.30 g of sodium borohydride are added in portions to a solution of 35.4 g of 3-hydroxy-7β-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester (crude product) in a mixture of 270 ml of dimethylformamide and 70 ml of glacial acetic acid in a stream of nitrogen while stirring and cooling with ice at approximately 15° to 20°. The reaction mixture is further stirred for one hour at room temperature, poured onto a mixture of ice and 2 N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed successively with 2 N hydrochloric acid, water, saturated, aqueous sodium bicarbonate solution and saturated, aqueous sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The residue is substantially freed from dimethylformamide under a high vacuum and recrystallised from ethyl acetate and a little diethyl ether. The title compound is obtained which has a melting point of 167°-170°; Rf~0.47 (silica gel; toluene/ethyl acetate 1:1); [α]D20 =+88°± 1° (in chloroform, c=0.526%); IR spectrum (in CH2Cl2): Absorption bands up to 3580; 3410; 1780; 1740; 1695; 1600; 1518; 1494 cm-1.

Workup

  1. temperaturecooling with ice at approximately 15° to 20°
  2. stirringThe reaction mixture is further stirred for one hour at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed successively with 2 N hydrochloric acid, water
  5. dry with materialsaturated, aqueous sodium bicarbonate solution and saturated, aqueous sodium chloride solution, dried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-485b8042772c4f219c9c5ac0b2b29b55
Source dataset
uspto-grants-1981_11
Patent number
US04301279

Reaction notes

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