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

HRID 1463100Notes

Reaction equation

HRID 1463100 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-e709e32318744971ba7af458423d4b0b
Source dataset
uspto-grants-1984_07
Patent number
US04462999

Reaction notes

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