Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-methyl-3-cephem-4-carboxylic acid

HRID 255787Notes

Reaction equation

HRID 255787 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:26][O:27][CH2:28][CH2:29][NH:30]C(OC(C)(C)C)=O)[C:10]([NH:12][CH:13]2[C:24](=[O:25])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([CH3:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:26][O:27][CH2:28][CH2:29][NH2:30])[C:10]([NH:12][CH:13]2[C:24](=[O:25])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([CH3:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317153177-[2-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-methyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317153187-[2-(2-Aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-methyl-3-cephem-4-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-methyl-3-cephem-4-carboxylic acid (syn isomer, 1.9 g.), conc. hydrochloric acid (1.4 g.) and methanol (30 ml.) was treated in a similar manner to that of Example 21-(2) to give 7-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-methyl-3-cephem-4-carboxylic acid (syn isomer, 1.3 g.).

Workup

  1. additionwas treated in a similar manner to that of Example 21-(2)

Sources & evidence

ORD record
ord-8ce3e9268ef64ef4900c0988d0873ff4
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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