Hydroquinone → 7-Amino-3-acetylthiomethyl-ceph-3-eme-4-carboxylic acid

HRID 839925Notes

Reaction equation

HRID 839925 reaction equation
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.C1(C=CC(O)=CC=1)O.C(=O)(O)[O-].[Na+].[C:32]([O-:35])(=[S:34])[CH3:33].[K+]>C(O)(=O)C.O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:34][C:32](=[O:35])[CH3:33])[CH2:15][S:14][C@H:9]12

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 23670855Potassium ethanethioate

Product 1

HCID 886008887-Amino-3-acetylthiomethyl-ceph-3-eme-4-carboxylic acidYield 85.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5.44 g of 7-amino-cephalosporanic acid and 50 ml of water with 1% hydroquinone was stirred under an inert atmosphere and 1.7 g of sodium bicarbonate were added thereto. After dissolution occurred, 3 g of potassium thioacetate were added thereto and the mixture was heated for 3 hours at 60° C and then was cooled. The mixture was acidified with acetic acid and stirred at room temperature and then vacuum filtered. The recovered product was washed and dried to obtain 4.9 g of 7-amino-3-acetylthiomethyl-ceph-3-eme-4-carboxylic acid.

Workup

  1. additionwere added
  2. dissolutionAfter dissolution
  3. temperaturewas cooled
  4. filtrationvacuum filtered
  5. washThe recovered product was washed
  6. customdried

Sources & evidence

ORD record
ord-2a33edd048554847ba4eafbe4a26731a
Source dataset
uspto-grants-1978_06
Patent number
US04097595

Reaction notes

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