(αZ)-2-Amino-α-[[2-(1,1-dimethylethoxy)-1,1-dimethyl-2-oxoethoxy]imino]-4-thiazoleacetic acid

Solid

33.1 g of (Z)-2-Amino-alpha-[1-(tert-butoxycarbonyl)]-1-methylethoxyimino-4-thiazolacetic acid(or may be side chain acid )and 41.8 g of DM were added to a 350 ml benzene-acetonitrile mother liquor at 22° C, then 4 ml of pyridine and 0.4 ml of N, N-dimethylaniline were added, the temperature was lowered to 18° C and 23 ml of Triethylphosphitewas added dropwise. The drop wise addition time was 1h40min. Using a microwave reactor, the microwave temperature was adjusted to 25° C, the microwave radiation power was 200 W, and the irradiation time was 30 min. temperature was cool down below 10°C, and subjected suction filtration to obtain crude product. The crude product was bubble-washed for 1 h in 150 ml of methanol at 23.5° Cto obtain the purified active ester, with a yield of 98.5percent and a purity of 99.1percent.At 21 ° C, 35g cefotaxime side chain acid and 48gDMWas added to a mixture of dichloro and acetonitrile (the mass of the mixture was 250 g and the density was 1.0 g / cm 3)After stirring for 10 min, 1.0 mL of pyridine was added, At 22 ° C, triethylamine (8.0 mL)After the addition was completed, the temperature was raised to 30 ° C., the reaction was incubated for 50 minutes, cooled, 28 ml of triethyl phosphite was added dropwise at 21 ° C, Drop when the process of sharing 2.5h, After the addition was completed, the reaction was incubated at 21 ± 1 ° C for 3.0 h, Then cooled to 3 incubated reaction 30min, suction filtration, And dried at 60 to ceftazidime side chain acid active ester, the yield was 92.6percentThe content is 99.3percent.

(Z)-2-(2-Aminothiazol-4-yl)-2-[(1-tert-butoxycarbonyl-1-methylethoxy)imino]acetic acid is an intermediate used in the process for the manufacture of Ceftazidime (C244100).

Molecular Weight:329.37
XLogP3:2.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:7
Exact Mass:329.10454189
Monoisotopic Mass:329.10454189
Topological Polar Surface Area:152
Heavy Atom Count:22
Complexity:473
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes