1-Iodo-2-methylpropyl 3-methylbutyrate → 1-(3-Methylbutyryloxy)-2-methylpropyl 7beta-[2-(2-aminothiazol-4-yl)acetamido]-3-acetoacetoxymethyl-ceph-3-em-4-carboxylate

HRID 4261Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O-:28])=[O:27])=[C:15]([CH2:18][O:19][C:20](=[O:25])[CH2:21][C:22]([CH3:24])=[O:23])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[CH3:32][CH:33]([CH3:43])[CH2:34][C:35]([O:37][CH:38](I)[CH:39]([CH3:41])[CH3:40])=[O:36]>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O:28][CH:38]([O:37][C:35](=[O:36])[CH2:34][CH:33]([CH3:43])[CH3:32])[CH:39]([CH3:41])[CH3:40])=[O:27])=[C:15]([CH2:18][O:19][C:20](=[O:25])[CH2:21][C:22]([CH3:24])=[O:23])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

Conditions

Temperature: -5 °C

Procedure

In 30 ml of N,N-dimethylformamide is dissolved 4.76 g of sodium 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-acetoacetoxymethyl-ceph-3-em-4-carboxylate and the solution is cooled to -5° C. With stirring, 5.0 g of 1-iodo-2-methylpropyl 3-methylbutyrate is added dropwise, followed by stirring for further 5 minutes. Thereafter, following the procedupe of Example 1, 2.5 g of the title compound is obtained.

Workup

stirringby stirring for further 5 minutes

Sources & evidence

ORD record: ord-14d0b639897e4843a7bf6d6a18bfd472
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04725592

Reaction notes

Loading…