ChemicalBook CAS DataBase List (Z)-2-(2-Aminothiazole-4-yl-)-2-trityloxyimino acetic acid

(Z)-2-(2-Aminothiazole-4-yl-)-2-trityloxyimino acetic acid synthesis

5synthesis methods

Product Name:(Z)-2-(2-Aminothiazole-4-yl-)-2-trityloxyimino acetic acid
CAS Number:128438-01-7
Molecular formula:C24H19N3O3S
Molecular Weight:429.49

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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(Z)-2-(2-Aminothiazole-4-yl-)-2-trityloxyimino acetic acid

128438-01-7
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$45.00/50mg

Yield: 90.3%

Reaction Conditions:

Stage #1:ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate with water;potassium hydroxide in ethanol at 20 - 30;Reflux;
Stage #2: with acetic acid in ethanol;water; pH=4 - 5

Steps:

2
Example 2Preparation of (Z)-(2-aminothiazol-4-yl)triphenylmethyloxyiminoacetic acid 97.5 mL of water and 1 1.25 g (0.170 mol) of KOH were charged into a reactor at 25 +/- 5 °C. Then 39 g (0.085 mol) of the ethyl (Z)-(2-aminothiazol-4-yl)triphenylmethyloxyiminoacetate obtained in Example 1 and 97.5 mL of ethanol were added at 25 +/- 5 °C. The reaction mixture was refluxed at 70 °C until the ethyl (Z)-(2-aminothiazol-4-yl)triphenylmethyloxyiminoacetate reached <1.0 area% on HPLC (about 3.5 h). The mixture was cooled to 10 °C and 97.5 mL of water was added. Then 15.36 g of acetic acid was added to adjust the pH within the range of 4 to 5. The product was filtered and washed four times with 97.5 mL of water and once with 97.5 mL of ethanol. The product was dried for 15 h at 60 °C and 25 mbar to obtain 32.4 g of the title product as a light yellow solid (96.07% HPLC purity, 90.3% yield). NMR (400 MHz, DMSO-efe): 6 = 6.69 (s, 1H), 7.23-7.35 (m, 17H).

References:

LONZA LTD;DAI, Danmei;ZHU, Wei;WANG, Siming WO2011/29596, 2011, A1 Location in patent:Page/Page column 7

76-83-5 Synthesis