Sodium → 7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[5-(4-tert-butylphenyl)thiadiazol-4-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1651187Notes

Reaction equation

HRID 1651187 reaction equation
CC(O[CH2:5][C:6]1[CH2:27][S:26][C@@H:9]2[C@H:10]([NH:13][C:14](/[C:16](/[C:20]3[N:24]=[C:23]([NH2:25])[S:22][CH:21]=3)=[N:17]\[O:18][CH3:19])=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:28]([OH:30])=[O:29])=O.[Na].[CH3:32][C:33]([C:36]1[CH:41]=[CH:40][C:39]([C:42]2[S:46][N:45]=[N:44][C:43]=2[SH:47])=[CH:38][CH:37]=1)([CH3:35])[CH3:34].[K]>O>[NH2:25][C:23]1[S:22][CH:21]=[C:20](/[C:16](=[N:17]/[O:18][CH3:19])/[C:14]([NH:13][CH:10]2[C:11](=[O:12])[N:8]3[CH:9]2[S:26][CH2:27][C:6]([CH2:5][S:47][C:43]2[N:44]=[N:45][S:46][C:42]=2[C:39]2[CH:40]=[CH:41][C:36]([C:33]([CH3:35])([CH3:34])[CH3:32])=[CH:37][CH:38]=2)=[C:7]3[C:28]([OH:30])=[O:29])=[O:15])[N:24]=1

Participants

6

Reactant 4

HCID 5360545SodiumHCID 5462222PotassiumHCID 5742673CefotaximeHCID 14294241HCID 14294241, compound

Product 1

HCID 885956607-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[5-(4-tert-butylphenyl)thiadiazol-4-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 12.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.5 g of Cefotaxime, sodium salt, 0.4 g of 5-[4-(1,1-dimethylethyl)phenyl]-1,2,3-thiadiazole-4-thiol, potassium salt and 16 ml of water was heated at 70° C. for 5.5 hours with pH adjustment to 6.8-7.2, then cooled and filtered. The filtrate was adjusted to pH 5 and extracted with 30 ml of ethyl acetate. The aqueous remainder was filtered through diatomaceous earth and adjusted to pH 2.5 with 2N hydrochloric acid. The resulting solid was collected, washed with water and dried, giving 86 mg of the desired product as a light orange solid [α]D26 =-10°+2 (0.885 DMSO): IR(KBr) 1770 cm-1 (β-lactam --C=O).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. extractionextracted with 30 ml of ethyl acetate
  4. filtrationThe aqueous remainder was filtered through diatomaceous earth
  5. customThe resulting solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-57b817eb2656427a83ad54bff5d74512
Source dataset
uspto-grants-1990_05
Patent number
US04927922

Reaction notes

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