7-Aminocephalosporanic acid → HCID 15093273, compound

HRID 1534781Notes

Reaction equation

HRID 1534781 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.[SH:24][C:25]1[S:29][CH:28]=[N:27][C:26]=1[C:30]([O:32][CH3:33])=[O:31]>O>[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:24][C:25]3[S:29][CH:28]=[N:27][C:26]=3[C:30]([O:32][CH3:33])=[O:31])[CH2:20][S:19][C@H:14]12

Participants

5

Reactant 3

HCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 15093269Methyl 5-sulfanyl-1,3-thiazole-4-carboxylate

Product 1

HCID 15093273HCID 15093273, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.7 g (2 eq.) of sodium hydrogencarbonate were added to a suspension of 2.7 g (10 mmol) of 7-ACS in 20 ml of water and 1.7 g (10 mmol) of methyl 5mercapthothiazole-4carboxylate (Preparation Example 5) were added after dissolution. The solution was then kept at 65° C. for 5 h and extracted twice with ethyl acetate after cooling. The aqueous phase was then acidified to pH 3 and the precipitated product was filtered off with suction and dried. 2.6 g (68%) of the desired title compound were obtained.

Workup

  1. additionwere added
  2. dissolutionafter dissolution
  3. extractionextracted twice with ethyl acetate
  4. temperatureafter cooling
  5. filtrationthe precipitated product was filtered off with suction
  6. customdried

Sources & evidence

ORD record
ord-12e97104ac0745ba913f5312dc1065ff
Source dataset
uspto-grants-1992_02
Patent number
US05091382

Reaction notes

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