Hydrochloric Acid → 2-(2-Aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetic acid

HRID 2412769Notes

Reaction equation

HRID 2412769 reaction equation
C([O:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:20]1[N:21]=[C:22]([NH2:25])[S:23][CH:24]=1)[C:15]([O:17]CC)=[O:16])(=O)C1C=CC=CC=1.[OH-].[Na+].CO.Cl>O1CCCC1>[OH:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:20]1[N:21]=[C:22]([NH2:25])[S:23][CH:24]=1)[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 53954764Ethyl 2-(2-aminothiazol-4-yl)-2-(2-benzoyloxyethoxyimino)acetate

Product 1

HCID 544034702-(2-Aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetic acidYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-(2-benzoyloxyethoxyimino)-2-(2-aminothiazol-4-yl)acetate (syn isomer) (8.5 g.), 1N aqueous sodium hydroxide (35 ml.), methanol (40 ml.) and tetrahydrofuran (40 ml.) was stirred at 35° to 40° C. for 9 hours and at ambient temperature for 12 hours. After adjusting the resultant solution to pH 6.5 with conc. hydrochloric acid, the solution was concentrated to about 2/3 volume of the initial. The concentrate was adjusted to pH 3.5 with conc. hydrochloric acid under ice-cooling, and the precipitates were collected by filtration, washed with water and acetone in turn and then dried over phosphorus pentoxide under reduced pressure to give 2-(2-hydroxyethoxyimino)-2-(2-aminothiazol-4-yl)acetic acid (syn isomer) (3.3 g.).

Workup

  1. concentrationthe solution was concentrated to about 2/3 volume of the initial
  2. temperaturecooling
  3. filtrationthe precipitates were collected by filtration
  4. washwashed with water and acetone in turn
  5. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-a17ca9bc47844ab1840d2e9bd01fe760
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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