Ethyl Acetate → 2-(2-Formamidothiazol-4-yl)-2-benzhydryloxycarbonylmethoxyiminoacetic acid

HRID 1494482Notes

Reaction equation

HRID 1494482 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=O)[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2].[NH2:14][O:15][CH2:16][C:17]([O:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(OCC)(=O)C>O.N1C=CC=CC=1.O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:14][O:15][CH2:16][C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 23358405Benzhydryl 2-aminooxyacetate

Product 1

HCID 536480482-(2-Formamidothiazol-4-yl)-2-benzhydryloxycarbonylmethoxyiminoacetic acidYield 98.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (2-formamidothiazol-4-yl)-glyoxylic acid (6.0 g) in water (60 ml) and pyridine (6 ml) was added a solution of benzhydryl 2-aminooxyacetate (9.0 g) in tetrahydrofuran (40 ml). The reaction mixture was stirred at ambient temperature for 3 hours. To the resultant solution was added ethyl acetate (200 ml). The separated organic layer was washed with 5% hydrochloric acid (100 ml), a saturated aqueous sodium bicarbonate and a saturated aqueous sodium chloride, and then dried over magnesium sulfate. The solvent was distilled off to give 2-(2-formamidothiazol-4-yl)-2-benzhydryloxycarbonylmethoxyiminoacetic acid (syn isomer) (13.0 g), mp 143°-151° C.

Workup

  1. washThe separated organic layer was washed with 5% hydrochloric acid (100 ml)
  2. dry with materiala saturated aqueous sodium bicarbonate and a saturated aqueous sodium chloride, and then dried over magnesium sulfate
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a75277b521e04e02ad159a4cc109d238
Source dataset
uspto-grants-1991_06
Patent number
US05026695

Reaction notes

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