2-TERT-BUTOXYCARBONYLAMINOTHIAZOLE-4-CARBOXYLIC ACID METHYL ESTER Chemical Properties

Melting point:

156-160

storage temp. 

2-8°C

Appearance

White to off-white Solid

InChI

InChI=1S/C10H14N2O4S/c1-10(2,3)16-9(14)12-8-11-6(5-17-8)7(13)15-4/h5H,1-4H3,(H,11,12,14)

InChIKey

VLJAUDDGOCGHFB-UHFFFAOYSA-N

SMILES

S1C=C(C(OC)=O)N=C1NC(OC(C)(C)C)=O

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2934100090

2-TERT-BUTOXYCARBONYLAMINOTHIAZOLE-4-CARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Uses

N-Boc Methyl 2-Aminothioazole-4-carboxylate a thiazolopyrimidinone derivative used as a modulator of NMDA receptor activity. Also a potential antiviral agent.

Synthesis

General procedure for the synthesis of methyl 2-(Boc-amino)thiazole-4-carboxylate from methyl 2-aminothiazole-4-carboxylate and di-tert-butyl dicarbonate: to a 1:1 dichloromethane/tetrahydrofuran (200mL) solution containing methyl 2-aminothiazole-4-carboxylate (10.0g, 63.22mmol, prepared as described in Example 3, Step 2), was added di-tert-butyl dicarbonate butyl ester (15.2 g, 69.64 mmol) and 4-(dimethylamino)pyridine (1.5 g, 12.30 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was partitioned between ethyl acetate and 10% w/v citric acid aqueous solution. The organic layer was separated, washed sequentially with water and brine, and then dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the crude product was purified by silica gel column chromatography to afford methyl 2-(tert-butoxycarbonylamino)thiazole-4-carboxylate as an oil (15.5 g, 95% yield) using 2:3 ethyl acetate/hexane as eluent.

References

[1] Patent: US2006/63814, 2006, A1. Location in patent: Page/Page column 61
[2] Patent: WO2015/52226, 2015, A1. Location in patent: Paragraph 0487
[3] Patent: WO2014/37480, 2014, A1. Location in patent: Page/Page column 125; 126

2-TERT-BUTOXYCARBONYLAMINOTHIAZOLE-4-CARBOXYLIC ACID METHYL ESTER(850429-62-8)Related Product Information

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