Sodium Iodide → 1-Pivaloyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 1463048Notes

Reaction equation

HRID 1463048 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O-:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:27]([O:33][CH:34](I)[CH3:35])(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29].[I-].[Na+]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O:20][CH:34]([O:33][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH3:35])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 133930641-Iodoethyl 2,2-dimethylpropanoateHCID 131712445Sodium 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Product 1

HCID 1317136091-Pivaloyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Procedure

In the same manner as Example 1, sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer) was reacted with 1-iodoethyl pivalate in the presence of sodium iodide to give 1-pivaloyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer), mp 110°-115° C. (decompn.).

Sources & evidence

ORD record
ord-9a049e1ad77b4511880f0850f2f2ac16
Source dataset
uspto-grants-1984_07
Patent number
US04463002

Reaction notes

Loading…