Ethyl 2-methoxyimino-2-(2-aminothiazol-4-yl)acetate hydrobromide → 2-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid

HRID 1089978Notes

Reaction equation

HRID 1089978 reaction equation
Br.[CH3:2][O:3][N:4]=[C:5]([C:11]1[N:12]=[C:13]([NH2:16])[S:14][CH:15]=1)[C:6]([O:8]CC)=[O:7]>[OH-].[Na+].O>[CH3:2][O:3][N:4]=[C:5]([C:11]1[N:12]=[C:13]([NH2:16])[S:14][CH:15]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 73668749Ethyl 2-methoxyimino-2-(2-aminothiazol-4-yl)acetate hydrobromide

Product 1

HCID 1252162-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acidYield 79.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate hydrobromide (anti isomer) (15.5 g.) was dissolved in a solution of sodium hydroxide (4.4 g.) in water (150 ml.) and the resulting solution was stirred for 1 hour at ambient temperature. An insoluble material was filtered off and the filtrate was adjusted to pH 5.0 to precipitate crystals. The crystals were collected by filtration and dried to give 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetic acid (anti isomer) (8.0 g.).

Workup

  1. filtrationAn insoluble material was filtered off
  2. customto precipitate crystals
  3. filtrationThe crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-101fb38f1fe147f492548973c1774c8b
Source dataset
uspto-grants-1992_01
Patent number
US05079369

Reaction notes

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