Carbonic Acid 4-Nitrophenyl 5-Thiazolylmethyl Este

English synonyms

5-(p-NitrophenoxycarbonyloxyMethyl);[(5-Thiazol)Methyl]-(4-nitrophenyl)carbonate;
((5-thiazolyl)Methyl)-(4-nitrophenyl)carbonate(SC);NCT;4-Nitrophenyl(thiazol-5-ylMethyl)
carbonateChemicalbook;((5-Thiazolyl)methyl)-(4-nitrophenyl)carbote;
carbonicacid4-nitrophenyl5-thiazolylmethylester;
RITONAVIRINTERMEDIATE-ATHIOZOLE[CARBONICACID-4NITROPHENYL-5-THIAZOLYLMETHYLESTER(NCT)

CAS number

144163-97-3

Molecular formula

C11H8N205S

Molecular weight

280.26

EINECS number

680-587-3

Melting point

65-67℃

Boiling point

475.3±45.0°℃(Predicted)

Density

1.485

Storage conditions

Keep in dark place,Sealed in dry,2-8℃

Solubility

Soluble in chloroform, ethyl acetate (a small amount)

Form

Solid

Acidity coefficient (pKa)

1.86±0.10 (Predicted)

Color

Light yellow low

InChl

InChl=1S/C11H8N205S/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

InChlKey

FTEKBGGQRNJIPQ-UHFFFAOYSA-N

SMILES

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

CAS database

144163-97-3(CAS DataBase Reference)

Use

((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate is used as a ritonavir intermediate.

Production Methods

General steps for synthesizing ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate (Compound 9) using 5-hydroxymethylthiazole (Compound 8, 17mmol)
and di(p-nitrobenzene)carbonate (Compound 7, 19mmol) as raw materials: Compound 7 is added to a dichloromethane (DCM, 40mL) solution of Compound 8,
followed by triethylamine (26mmol). The reaction mixture is stirred at room temperature for 12 hours and concentrated under reduced pressure after the reaction is completed.
The concentrated mixture is diluted with ethyl acetate (EtOAc) and washed with saturated sodium carbonate (Na2CO3) aqueous solution, water and brine in sequence.
After washing, the organic solvent is removed under reduced pressure. The residue is purified by flash column chromatography (silica gel as the stationary phase,
the eluent ratio is hexane/ethyl acetate = 1/1) to finally obtain Compound 9 (4.7g).

Upstream raw materials

5-hydroxymethylthiazole, di(p-nitrobenzene) carbonate, triethylamine, dichloromethane

Downstream products

N-[(1R,4R)-4-amino-5-phenyl-1-(benzyl)pentyl]carbamic acid 5-thiazolylmethyl ester