2-Amino-α-oxo-4-thiazoleacetic acid

2-(2-aminothiazol-4-yl)-2-oxoacetic acid (Y) (10.00 g, 47.93 mmol) and compound W (R2 = CH(Ph)2) (13.31g, 46.98 mmol) were suspended in DMAC (40 mL), followed by addition of triethylamine (5.01 mL, 35.95 mmol). The reaction mixture was stirred at 20 C for 5 h. HPLC showed completion of the reaction, and Z/E = 97/3. To the reaction mixture was added water (120 mL) with stirring. The mixture was stirred for 20 mm to obtain a suspension. The suspension was filtered and the filter cake was washed with water (50 mL). The filter cake was slurried in a combined solvent of THF/ethyl acetate (50 mL / 50 mL) at 60 C and cooledto 20 C. The solid was filtered and dried at 50 C for 3 h to get 3 (R2 = CH(Ph)2) (19.5 g, 88% yield). 1H NMR (400 MHz, DMSO-d6) O ppm 1.37 -1 .42 (m, 2 H) 1.44 - 1.49 (m, 2 H) 6.87 (5, 1 H) 6.94 (5, 1 H) 7.22- 7.30 (m, 6 H) 7.45 - 7.49 (m, 4 H).This compound was then treated at 20C with a solution of 2-amino-4-thiazoleglyoxylic acid (2.61 g, 15.2 mmole) in dimethylformamide (50 ml), followed by 5 ml of water. The reaction was stirred at 20C for 20 hours, and was then chilled and diluted with 250 ml of water. Stirring of the resulting gum gave a granular solid which was filtered, washed with water, and then azeotroped with acetonitrile to dryness. The dry solid was slurried with 100 ml of acetonitrile, filtered, and finally washed sequentially with acetonitrile, ethyl ether, and hexane. Drying in air gave 1.97 g of the title compound.(A) (2-Amino-4-thiazolyl)glyoxylic acid [2-(Formylamino)-4-thiazolyl]glyoxylic acid (10 g, 0.05 mol) suspended in methanol (100 ml) was combined with concentrated hydrochloric acid (6.25 ml, 0.075 mol) and stirred overnight at room temperature causing dissolution of the solid. After filtration to remove a small amount of insoluble material, solvent was removed in vacuo. The residue was suspended in water and the pH was adjusted to 2 with potassium hydroxide solution. The solid was collected by filtration, washed with water, then twice with acetone, followed by two washings with ether, giving 4.21 g of a powder. A second crop was obtained by concentrating the filtrate, lowering the pH to 0.8, and collecting and washing as above to obtain 3.74 g of a powder. Both crops were the hydrochloride salt of the title compound. They were dissolved in water at pH 7-8, the pH was then lowered to pH 3.1-3.3, the precipitate was collected, washed twice with acetone, then twice with ether yielding 5.96 g of the title compound.(c) 2-Amino-alpha-[(1H-imidazole-2-yl-methoxy)imino]-4-thiazole acetic acid, hydrochloride (1:2) (Z) 2 g of 2-[(aminoxy)methyl]-1H-imidazolehydrochloride (1:2) from example 1(b) and 2.24 g 2-amino-thiazol-4-glyoxylic acid are suspended with stirring in 50 ml H2 O. The pH is adjusted with potassium carbonate to 6 and stirring is continued for 12 hours. The pH is then adjusted to 6.4 with hydrochloric acid. After 2 hours 0.8 of crystalline 2-amino-alpha-[(1H-imidazol-2-yl-methoxy)imino]-4-thiazole acetic acid hydrochloride (1:2) is filtered off with a melting point of 158-160 C. (dec.).EXAMPLE 3 To 10.1 g of 2-(2-aminothiazol-4-yl)thioglyoxylic S-acid methyl ester and 80 ml of water was added 10.6 g of sodium carbonate with ice-cooling, and the resulting mixture was stirred at the same temperature for 1 hour. Subsequently, the thus obtained reaction mixture was adjusted to pH 2.5 with 6 N hydrochloric acid at the same temperature. The deposited crystals were collected by filtration, washed with water, and then dried to obtain 6.2 g (67.8% yield) of 17. The starting material was prepared by reaction of O-(1-methylimidazol-2-yl)methylhydroxylamine with

Used as cephalosporin intermediate

Molecular Weight:172.16
XLogP3:0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:171.99426317
Monoisotopic Mass:171.99426317
Topological Polar Surface Area:122
Heavy Atom Count:11
Complexity:196
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes