Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)-acetamido]-3-chloro-3-cephem-4-carboxylic acid

HRID 1905274Notes

Reaction equation

HRID 1905274 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:26][O:27][CH2:28][C:29]([F:32])([F:31])[F: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]([Cl: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][C:29]([F:30])([F:32])[F:31])[C:10]([NH:12][CH:13]2[C:24](=[O:25])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317124877-[2-(2-Formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylic acid

Product 1

HCID 1317124887-[2-(2-Aminothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)-acetamido]-3-chloro-3-cephem-4-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-[2-(2-Formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 0.7 g.), conc. hydrochloric acid (0.43 ml.) and methanol (16 ml.) were treated in a similar manner to that of Example 21-(3) to give 7-[2-(2-aminothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)-acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 0.65 g.)

Sources & evidence

ORD record
ord-19435a1e25aa47c9a94e80ed6ddcff49
Source dataset
uspto-grants-1989_06
Patent number
US04841062

Reaction notes

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