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

HRID 1650535Notes

Reaction equation

HRID 1650535 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][C:28]([F:31])([F:30])[F:29])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.O1CCCC1>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][C:28]([F:29])([F:31])[F:30])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 1317124807-[2-(2-Formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317124817-[2-(2-Aminothiazol-4-yl)-2(2,2,2-trifluoroethoxyimino)acetamido]-3-cephem-4-carboxylic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.5 g.), conc. hydrochloric acid (1.3 ml.), tetrahydrofuran (10 ml.) and methanol (30 ml.) was 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-cephem-4-carboxylic acid (syn isomer, 1.1 g.).

Workup

  1. additionwas treated in a similar manner to that of Example 21-(3)

Sources & evidence

ORD record
ord-396180ee8eda4571a4f881ecb584cedb
Source dataset
uspto-grants-1990_05
Patent number
US04923998

Reaction notes

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