2-t-Butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid → 4-Nitrobenzyl 7-[2-(tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylate

HRID 647459Notes

Reaction equation

HRID 647459 reaction equation
Cl.[NH2:2][CH:3]1[C:25](=[O:26])[N:5]2[C:6]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])=[C:7]([O:10][CH3:11])[CH2:8][S:9][C@H:4]12.[C:27]([O:31][C:32]([CH2:34][O:35][N:36]=[C:37]([C:41]1[N:42]=[C:43]([NH:46][CH:47]=[O:48])[S:44][CH:45]=1)[C:38](O)=[O:39])=[O:33])([CH3:30])([CH3:29])[CH3:28]>>[C:27]([O:31][C:32]([CH2:34][O:35][N:36]=[C:37]([C:41]1[N:42]=[C:43]([NH:46][CH:47]=[O:48])[S:44][CH:45]=1)[C:38]([NH:2][CH:3]1[C:25](=[O:26])[N:5]2[C:6]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)=[O:13])=[C:7]([O:10][CH3:11])[CH2:8][S:9][C@H:4]12)=[O:39])=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 543909512-t-Butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acidHCID 703620084-Nitrobenzyl 7-amino-3-methoxy-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 1317131354-Nitrobenzyl 7-[2-(tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylateYield 100.4%

Procedure

4-Nitrobenzyl 7-amino-3-methoxy-3-cephem-4-carboxylate hydrochloride (4.02 g) and 2-(tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer, 3.62 g) were treated in a similar manner to to that of Example 1 to give 4-nitrobenzyl 7-[2-(tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylate (syn isomer, 6.8 g).

Sources & evidence

ORD record
ord-a23a21eb642246628b59fe1fa1139438
Source dataset
uspto-grants-1983_10
Patent number
US04409217

Reaction notes

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