Hydrochloric Acid → 2-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid

HRID 1284666Notes

Reaction equation

HRID 1284666 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)[C:5]([O:7]CC)=[O:6].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

Product 1

HCID 1252162-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acidYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N.M.R. δppm (CDCl3): 6.72 (1H, s), 5.91 (2H, broad s), 4.38 (2H, q, J=7 Hz), 4.03 (3H, s), 1.38 (3H, t, J=7 Hz). (4) Ethanol (10 ml.) was added to a suspension of ethyl 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (2.2 g.) in a 1N aqueous solution of sodium hydroxide (12 ml.) and the mixture was stirred for 15 hours at ambient temperature. The reaction mixture was adjusted to pH 7.0 with 10% hydrochloric acid and ethanol was distilled off under reduced pressure. The residual aqueous solution was washed with ethyl acetate, adjusted to pH 2.8 with 10% hydrochloric acid and stirred under ice-cooling to precipitate crystals. The crystwere collected by filtration, washed with acetone and recrystallized from ethanol to give colorless needles of 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetic acid (syn isomer) (1.1 g.)

Workup

  1. distillationwas distilled off under reduced pressure
  2. washThe residual aqueous solution was washed with ethyl acetate
  3. stirringstirred under ice-
  4. temperaturecooling
  5. customto precipitate crystals
  6. filtrationThe crystwere collected by filtration
  7. washwashed with acetone
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-13f17e647eca49fc81093778d28f6a60
Source dataset
uspto-grants-1986_01
Patent number
US04563522

Reaction notes

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