Acetonitrile → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(imidazo[1,5-a]pyridin-2-ium-2-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1111441Notes

Reaction equation

HRID 1111441 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH3:27])/[C:8]([NH:10][C@@H:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18]O)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[CH:28]1[N:29]=[CH:30][N:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=12.C(#N)C.P(OCC)(OCC)OCC>C(N)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH3:27])/[C:8]([NH:10][C@@H:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH2:18][N+:29]4[CH:28]=[C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][N:31]5[CH:30]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 31215Triethyl phosphiteHCID 274090Imidazo(1,5-a)pyridineHCID 9576239Desacetylcefotaxime

Product 1

HCID 5487130(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(imidazo[1,5-a]pyridin-2-ium-2-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Conditions

Temperature
22.5 °C

Procedure

In 1 ml of formamide were dissolved 413 mg of 7β-[2-(2-aminothiazole-4-yl)-2-(Z)-methoxyiminoacetamido]-3-hydroxymethyl-3-cephem-4 -carboxylic acid and 354 mg of imidazo[1.5-a]pyridine. To the solution were added 1 ml of acetonitrile and 0.86 ml of triethyl phosphite, and the mixture was stirred at 20 to 25° C. for 10 hours. The resultant product was treated by the manner of Example 32 to give 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-(imidazo [1,5-a]pyridinium-2-yl)methyl-3-cephem-4-carboxylate.

Sources & evidence

ORD record
ord-42e61d4f21b443d6a170ba3a102d56ef
Source dataset
uspto-grants-1990_12
Patent number
US04980464

Reaction notes

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