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

2-TERT-BUTOXYCARBONYLAMINOTHIAZOLE-4-CARBOXYLIC ACID METHYL ESTER Property

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

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2934100090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

2-TERT-BUTOXYCARBONYLAMINOTHIAZOLE-4-CARBOXYLIC ACID METHYL ESTER Chemical Properties,Usage,Production

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