Sodium Carbonate → 7beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 126900Notes

Reaction equation

HRID 126900 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Cl:24])=[C:5]([C:7](=O)[C:8]([NH:10][C@@H:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.Cl.[CH3:26][O:27][NH2:28].C(=O)([O-])[O-].[Na+].[Na+]>CO>[NH2:1][C:2]1[S:3][C:4]([Cl:24])=[C:5]([C:7](=[N:28][O:27][CH3:26])[C:8]([NH:10][C@@H:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 1317121037beta-[2-(2-Amino-5-chloro-4-thiazolyl)glyoxylylamino]-3-cephem-4-carboxylic acid

Product 1

HCID 1317121027beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar procedure to that of Example 2-1, 7β-[2-(2-amino-5-chloro-4-thiazolyl)glyoxylylamino]-3-cephem-4-carboxylic acid (276 mg) is treated with methoxyamine hydrochloride (58 mg) in methanol (5 ml) in the presence of sodium carbonate (74 mg) to afford 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid. Similarly prepared are compounds of Table 1.

Sources & evidence

ORD record
ord-e325f3f41ac94083878ccdf7cde7b062
Source dataset
uspto-grants-1981_03
Patent number
US04254119

Reaction notes

Loading…