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

HRID 434385Notes

Reaction equation

HRID 434385 reaction equation
C(=O)(O)[O-].[Na+].CC(O[CH2:10][C:11]1[CH2:20][S:19][C@@H:14]2[C@H:15]([NH2:18])[C:16](=[O:17])[N:13]2[C:12]=1[C:21]([OH:23])=[O:22])=O.C1(C=CC(O)=CC=1)O.[C:32]([O-:35])(=[S:34])[CH3:33].[K+]>O.C(O)(=O)C>[NH2:18][CH:15]1[C:16](=[O:17])[N:13]2[C:12]([C:21]([OH:23])=[O:22])=[C:11]([CH2:10][S:34][C:32](=[O:35])[CH3:33])[CH2:20][S:19][C@H:14]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

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

Workup

  1. dissolutionafter dissolution
  2. temperaturewas then cooled
  3. stirringThe mixture was stirred at room temperature
  4. filtrationfiltered
  5. washthe product was washed
  6. customdried

Sources & evidence

ORD record
ord-876ead24d428436e88213d751aafaea2
Source dataset
uspto-grants-1983_08
Patent number
US04396618

Reaction notes

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