((5-Thiazolyl)methyl)-(4-nitrophenyl)carbonate Chemical Properties

Melting point:

65-67°C

Boiling point:

475.3±45.0 °C(Predicted)

Density 

1.485

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform, Ethyl Acetate (Slightly)

form 

Solid

pka

1.86±0.10(Predicted)

color 

Pale Yellow

InChI

InChI=1S/C11H8N2O5S/c14-11(17-6-10-5-12-7-19-10)18-9-3-1-8(2-4-9)13(15)16/h1-5,7H,6H2

InChIKey

FTEKBGGQRNJIPQ-UHFFFAOYSA-N

SMILES

C(OCC1SC=NC=1)(=O)OC1=CC=C([N+]([O-])=O)C=C1

CAS DataBase Reference

144163-97-3(CAS DataBase Reference)

((5-Thiazolyl)methyl)-(4-nitrophenyl)carbonate Usage And Synthesis

Chemical Properties

Pale-Yellow Solid

Uses

Retinovir intermediate.

Synthesis

General procedure for the synthesis of ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate (compound 9) from 5-hydroxymethylthiazole (compound 8, 17 mmol) and bis(p-nitrophenyl)carbonate (compound 7, 19 mmol): compound 7 was added to a dichloromethane (DCM, 40 mL) solution of compound 8, followed by triethylamine (26 mmol) . The reaction mixture was stirred at room temperature for 12 h. After completion of the reaction it was concentrated under reduced pressure. The concentrated mixture was diluted with ethyl acetate (EtOAc) and washed sequentially with saturated aqueous sodium carbonate (Na2CO3) solution, water and brine. After washing, the organic solvent was removed under reduced pressure. The residue was purified by fast column chromatography (silica gel as stationary phase, eluent ratio hexane/ethyl acetate=1/1) to give the final compound 9 (4.7 g).

References

[1] Patent: WO2008/10921, 2008, A2. Location in patent: Page/Page column 188-189
[2] Patent: US2010/256366, 2010, A1. Location in patent: Page/Page column 19
[3] Patent: EP2231628, 2015, B1. Location in patent: Paragraph 0878
[4] Patent: US2018/30043, 2018, A1. Location in patent: Paragraph 0163

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