Acetic Acid → HCID 178459334, compound

HRID 358269Notes

Reaction equation

HRID 358269 reaction equation
[O:1]=[C:2]([CH2:24][CH3:25])[CH2:3][C:4]([NH:6][C@@H:7]1[C:22](=[O:23])[N:9]2[C:10]([C:19]([OH:21])=[O:20])=[C:11]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[CH2:12][S:13][C@H:8]12)=[O:5].C(O)(=O)C.[N:30]([O-])=[O:31].[Na+]>O>[OH:31][N:30]=[C:3]([C:2](=[O:1])[CH2:24][CH3:25])[C:4]([NH:6][C@@H:7]1[C:22](=[O:23])[N:9]2[C:10]([C:19]([OH:21])=[O:20])=[C:11]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[CH2:12][S:13][C@H:8]12)=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 131713660HCID 131713660, compound

Product 1

HCID 178459334HCID 178459334, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6 g. of benzhydryl ester of 7β-(3-oxovaleramido)-3-acetoxymethylceph-3-em-4-carboxylic acid in 20 ml. of glacial acetic acid are added dropwise 1.54 g. of sodium nitrite dissolved in 15 ml. of water, and the mixture is stirred for 2 hours at ambient temperature. The mixture is then diluted with 500 ml. of ethyl acetate and washed 3 times with 100 ml. of an aqueous saturated sodium chloride solution. The organic phase is made anhydrous and evaporated to dryness and the residue is triturated with diethyl ether. 5.5 g. of benzhydryl ester of 7β-(2-hydroxyimino-3-oxovaleramido)-3-acetoxymethylceph-3-em-4-carboxylic acid melting at 56°-62° C. are obtained.

Workup

  1. additionThe mixture is then diluted with 500 ml
  2. washof ethyl acetate and washed 3 times with 100 ml
  3. customevaporated to dryness
  4. customthe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-ba37d7d9c35c41559f0ceada402bb9da
Source dataset
uspto-grants-1984_08
Patent number
US04465831

Reaction notes

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