Hydrochloric Acid → 2-Ethoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid

HRID 2412764Notes

Reaction equation

HRID 2412764 reaction equation
C(=O)(O)[O-].[Na+].[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=O)[C:15]([OH:17])=[O:16])[N:13]=1)=[O:7].Cl.[NH2:20][O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>O>[CH2:26]([O:25][C:23]([CH2:22][O:21][N:20]=[C:14]([C:12]1[N:13]=[C:9]([NH:8][CH:6]=[O:7])[S:10][CH:11]=1)[C:15]([OH:17])=[O:16])=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 12283957Ethyl aminoxyacetate hydrochlorideHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acid

Product 1

HCID 544193372-Ethoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acidYield 47.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium bicarbonate (0.84 g.) was added to a suspension of 2-(2-formamidothiazol-4-yl)glyoxylic acid (2 g.) in water (120 ml.) to prepare a solution. Ethyl 2-aminooxyacetate hydrochloride (4.56 g.) was added to the solution and stirred at ambient temperature for 3 hours while adjusting a pH 6 with sodium bicarbonate. The resultant solution was adjusted to pH 1.5 with hydrochloric acid, salted out and extracted with ethyl acetate three times. The extract was dried over magnesium sulfate and concentrated in vacuo. The residue was pulverized with diethyl ether, and the precipitates were collected by filtration and dried to give 2-ethoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (1.44 g.), mp. 112° C. (dec.).

Workup

  1. customto prepare a solution
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationthe precipitates were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c071e9f5562c447ea74fb43704f831e7
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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