Water → HCID 53718133, compound

HRID 261689Notes

Reaction equation

HRID 261689 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][N:9]=[C:10]([C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].O>C(OCC)(=O)C.CN(C)C=O>[CH3:7][O:8][N:9]=[C:10]([C:16]1[N:17]=[C:18]([NH:21][C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:19][CH:20]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

Product 1

HCID 53718133HCID 53718133, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine (3 g.) was added to a solution of ethyl 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (6.5 g.) in a mixture of ethyl acetate (60 ml.) and dimethylformamide (20 ml.). To the solution was dropwise added with stirring at 4° C. ethyl chloroformate (8 g.). After adding water (50 ml.) to the reaction mixture, the organic layer was separated, washed with water and then with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel (120 g.) using a mixture of ether and petroleum ether (5:2) as an eluent to give ethyl 2-methoxyimino-2-(2-ethoxycarbonylamino-1,3-thiazol-4-yl)acetate (syn isomer) (5.4 g.).

Workup

  1. additionTo the solution was dropwise added
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride and dried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. additiona mixture of ether and petroleum ether (5:2) as an eluent

Sources & evidence

ORD record
ord-5aecdaf931344618ac74e97f949e838c
Source dataset
uspto-grants-1979_08
Patent number
US04166115

Reaction notes

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