Iodomethyl 2-ethylbutanoate → 2-Ethylbutyryloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 1463050Notes

Reaction equation

HRID 1463050 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]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[CH2:26]([CH:28]([CH2:34][CH3:35])[C:29]([O:31][CH2:32]I)=[O:30])[CH3:27]>C(N(CC)CC)C>[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][CH2:32][O:31][C:29](=[O:30])[CH:28]([CH2:34][CH3:35])[CH2:26][CH3:27])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 23449337Iodomethyl 2-ethylbutanoateHCID 1317124447-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317136112-Ethylbutyryloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In the same manner as Example 8, 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn-isomer) was reacted with iodomethyl 2-ethylbutyrate in the presence of triethylamine to give 2-ethylbutyryloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer).

Sources & evidence

ORD record
ord-ee4cbbb2543842ddaa8823d1dfe7759c
Source dataset
uspto-grants-1984_07
Patent number
US04463002

Reaction notes

Loading…