Hydrochloric Acid → 7-[2-Carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-methylthiomethyl-3-cephem-4-carboxylic acid

HRID 234192Notes

Reaction equation

HRID 234192 reaction equation
[C:1]([CH2:4][O:5][N:6]=[C:7]([C:26]1[N:27]=[C:28]([NH:31]C(=O)C(F)(F)F)[S:29][CH:30]=1)[C:8]([NH:10][CH:11]1[C:24](=[O:25])[N:13]2[C:14]([C:21]([OH:23])=[O:22])=[C:15]([CH2:18][S:19][CH3:20])[CH2:16][S:17][C@H:12]12)=[O:9])([OH:3])=[O:2].C([O-])(=O)C.[Na+].Cl>O>[C:1]([CH2:4][O:5][N:6]=[C:7]([C:26]1[N:27]=[C:28]([NH2:31])[S:29][CH:30]=1)[C:8]([NH:10][CH:11]1[C:24](=[O:25])[N:13]2[C:14]([C:21]([OH:23])=[O:22])=[C:15]([CH2:18][S:19][CH3:20])[CH2:16][S:17][C@H:12]12)=[O:9])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 131713154HCID 131713154, compound

Product 1

HCID 1317131537-[2-Carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-methylthiomethyl-3-cephem-4-carboxylic acidYield 52.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7-[2-carboxymethoxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-methylthiomethyl-3-cephem-4-carboxylic acid (syn isomer) (4.1 g) and sodium acetate (9.56 g) in water (41 ml) was stirred for 19.5 hours at ambient temperature. The resultant solution was adjusted to pH 2.0 with conc. hydrochloric acid. The precipitates were collected by filtration and dried over phosphorus pentoxide to give 7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-methylthiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.8 g), mp 173°-176° C. (dec.).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-2872558248e240aeae2767f85a4c0ab3
Source dataset
uspto-grants-1997_01
Patent number
US05594132

Reaction notes

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