tert-butyl thiazol-4-ylcarbamate Chemical Properties

Melting point:

153-155 °C

Boiling point:

254.9±13.0 °C(Predicted)

Density 

1.242±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.39±0.70(Predicted)

Appearance

White to off-white Solid

tert-butyl thiazol-4-ylcarbamate Usage And Synthesis

Uses

tert-butyl thiazol-4-ylcarbamate is an organic intermediate that can be prepared from thiazole-4-carboxylic acid via the Curtiss rearrangement reaction.

Synthesis

Under nitrogen protection, 5.80 mL (41.84 mmol) of triethylamine and 9.10 mL (42.19 mmol) of azido azide phosphate were sequentially added to a solution of 4.85 g (37.55 mmol) of thiazole-4-carboxylic acid dissolved in 180 mL of tert-butanol and the reaction mixture was cooled in an ice bath. Subsequently, the reaction system was heated to reflux for 16 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in dichloromethane and washed twice sequentially with water and saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate and concentrated. The resulting crude product was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate, 1:1, v/v) to afford 7.07 g (35.30 mmol, 94% yield) of N-Boc-4-aminothiazole as beige crystals.ESI-MS: m/e 201 ([M + H]+).

References

[1] Synthesis, 2010, # 18, p. 3152 - 3162
[2] Patent: US2012/252759, 2012, A1. Location in patent: Page/Page column 22
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 7029 - 7042
[4] Patent: WO2014/41175, 2014, A1. Location in patent: Page/Page column 57
[5] Patent: EP3375782, 2018, A1. Location in patent: Paragraph 0049; 0152; 0154

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