Hydrochloric Acid → 7-[2-(Tert-butoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylic acid

HRID 647463Notes

Reaction equation

HRID 647463 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:29]1[N:30]=[C:31]([NH:34]C=O)[S:32][CH:33]=1)[C:12]([NH:14][CH:15]1[C:27](=[O:28])[N:17]2[C:18]([C:24]([OH:26])=[O:25])=[C:19]([O:22][CH3:23])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>CO>[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:29]1[N:30]=[C:31]([NH2:34])[S:32][CH:33]=1)[C:12]([NH:14][CH:15]1[C:27](=[O:28])[N:17]2[C:18]([C:24]([OH:26])=[O:25])=[C:19]([O:22][CH3:23])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317131387-[2-(Tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylic acid

Product 1

HCID 1317131407-[2-(Tert-butoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylic acidYield 79.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-[2-(tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn isomer, 3.7 g), methanol (40 ml) and conc. hydrochloric acid (2.1 ml) were treated in a similar manner to that of Example 5 to give 7-[2-(tert-butoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn isomer, 2.8 g).

Sources & evidence

ORD record
ord-2d1d010e78cc468b8d810a99edeea361
Source dataset
uspto-grants-1983_10
Patent number
US04409217

Reaction notes

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