7-Aminocephalosporanic acid → Cefotaxime

HRID 1934794Notes

Reaction equation

HRID 1934794 reaction equation
SC1([CH:13](Br)[C:14](=O)/[C:15](=[N:19]/[O:20][CH3:21])/[C:16]([O-:18])=O)NN=C(C2C=CC=CC=2)O1.[NH2:24][C:25]([NH2:27])=[S:26].C([O-])(=O)C.[Na+].[CH3:33][C:34]([O:36][CH2:37][C:38]1[CH2:47][S:46][C@@H:41]2[C@H:42]([NH2:45])[C:43](=[O:44])[N:40]2[C:39]=1[C:48]([OH:50])=[O:49])=[O:35]>O1CCCC1.O.C(N(CC)CC)C>[CH3:33][C:34]([O:36][CH2:37][C:38]1[CH2:47][S:46][C@@H:41]2[C@H:42]([NH:45][C:16](/[C:15](/[C:14]3[N:24]=[C:25]([NH2:27])[S:26][CH:13]=3)=[N:19]\[O:20][CH3:21])=[O:18])[C:43](=[O:44])[N:40]2[C:39]=1[C:48]([OH:50])=[O:49])=[O:35]

Participants

8

Reactant 4

HCID 4413287-Aminocephalosporanic acidHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 178502847HCID 178502847, compound

Product 1

HCID 5742673Cefotaxime

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
10 °C

Procedure

2-Mercapto-5-phenyl-1,3,4-oxadiazolyl-(Z)-4-bromo-2-methoxyimino-3-oxo-butyrate (46.0 g) was taken in a mixture of tetrahydrofuran (250 ml) and water (150 ml). The solution was cooled to 10° C. and the thiourea (20.47 g) and sodium acetate (4.32 g) were added. The reaction mixture was stirred for 1.0 hr. 7-amino cephalosporanic acid (25.0 g) was added followed by slow addition of triethylamine (20.4 g) the progress of the reaction was monitored by HPLC. The reaction was completed in 6-8 hr. The reaction mixture was extracted with dichloromethane (3×200 ml). The aqueous layer was acidified with dil. HCl to obtain cefotaxime, 38.0 g.

Workup

  1. waitThe reaction was completed in 6-8 hr
  2. extractionThe reaction mixture was extracted with dichloromethane (3×200 ml)

Sources & evidence

ORD record
ord-dc4bda9ee94548d6abe29bd8dd929be9
Source dataset
uspto-grants-2002_05
Patent number
US06384215B1

Reaction notes

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