Hydrochloric Acid → 2-t-Butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid
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][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].Cl>O>[C: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])([CH3:29])([CH3:28])[CH3:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium bicarbonate (4.2 g.) was added to a suspension of 2-(2-formamidothiazol-4-yl)glyoxylic acid (10 g.) in water (500 ml.) to prepare a solution. t-Butyl 2-aminooxyacetate hydrochloride (8.1 g.) was added to the solution and stirred at ambient temperature for 3 hours while adjusting to 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-t-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (11.3 g.), mp. 117° C. (dec.).
Workup
- customto prepare a solution
- extractionextracted with ethyl acetate three times
- dry with materialThe extract was dried over magnesium sulfate
- concentrationconcentrated in vacuo
- filtrationthe precipitates were collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-ae3a1ee83a3947609f278af51133a670
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04493833
Reaction notes
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