Acetic Anhydride → HCID 68131831, compound

HRID 1605400Notes

Reaction equation

HRID 1605400 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:26])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:24][CH:23]=1.[C:1]([O:4][CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:26])[CH:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C@H:9]2[S:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12800574HCID 12800574, compound

Product 1

HCID 68131831HCID 68131831, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Using the method outlined in German Offenlegungschrift No. 2,103,014, 20.4 g of 3-acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid was dissolved in 60 ml of dry pyridine, with heating and then 6 ml of acetic anhydride was added to the cooled solution. The mixture solidified on standing for 2 hours. It was then diluted with 50 ml of pyridine and the solid filtered and washed with 150 ml of ethyl acetate. The product was recrystallized from 150 ml of ethyl acetate and 20 ml of alcohol to yield 15.4 g of 3-acetoxymethyl-7-(2-thienylacetamido)-2-cephem-4-carboxylic acid pyridine salt, mp 150°-151° d.

Workup

  1. temperaturewith heating
  2. filtrationthe solid filtered
  3. washwashed with 150 ml of ethyl acetate
  4. customThe product was recrystallized from 150 ml of ethyl acetate and 20 ml of alcohol

Sources & evidence

ORD record
ord-ef093cd4197c458bbeeb4687b1801d98
Source dataset
uspto-grants-1976_04
Patent number
US03950329

Reaction notes

Loading…