Ethyl 4-methyl-5-thiazoleactate Chemical Properties

Melting point:

28°C(lit.)

Boiling point:

233°C(lit.)

Density 

1.198±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to lump

pka

1.57±0.10(Predicted)

color 

White to Almost white

LogP

1.410 (est)

CAS DataBase Reference

20582-55-2(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

2934208090

Ethyl 4-methyl-5-thiazoleactate Usage And Synthesis

Uses

Ethyl 4-methylthiazolium-5-carboxylate is a key intermediate in the synthesis of cefditorenpivoxil. Cefditorenpivoxil was developed by Meiji Seika Co., Ltd. of Japan and launched in Japan in 1994 under the trade name Meiact. Cefditorenpivoxil has a broad antibacterial spectrum against both Gram-positive and Gram-negative bacteria.

Chemical Properties

white to light yellow crystal powde

Synthesis

General procedure for the synthesis of ethyl 4-methylthiazole-5-carboxylate from ethyl 2-amino-4-methylthiazole-5-carboxylate: compound 3a (4.0 g, 21.5 mmol) was dissolved in 106 mL of 30% hypophosphite (H3PO2) solution. The reaction system was cooled to -5°C, after which sodium nitrite (NaNO2, 3.0 g, 2.0 eq.) was dissolved in 12 mL of water and slowly added dropwise to the reaction solution. After the dropwise addition, the reaction mixture was transferred to 0°C and kept for 1 hour, then stirring was continued for 2 hours at room temperature. Subsequently, pre-cooled sodium hydroxide solution (17 g NaOH dissolved in 200 mL of water) was added slowly dropwise. The reaction mixture was adjusted to neutral with sodium bicarbonate (NaHCO3) solution and then extracted with ether (Et2O, 50 mL x 3). The organic phases were combined and purified by column chromatography (eluent ratio: petroleum ether:ethyl acetate = 50:1, v/v) to give the yellow semi-solid product 3b (2.1 g, 56% yield).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6231 - 6235
[2] Patent: CN101921268, 2016, B. Location in patent: Paragraph 0128; 0131; 0136-0139
[3] Tetrahedron, 2013, vol. 69, # 22, p. 4436 - 4444

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