O-Cresol → Ethyl (4-mercapto-2-methylphenoxy)acetate

HRID 1014070Notizen

Reaktionsgleichung

[CH3:1][C:2]1[CH:3]=[C:4]([S:13]CC2SC(C3C=CC(C(F)(F)F)=CC=3)=NC=2C)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([OH:12])=[O:11].[C:31]1(C)C(O)=CC=C[CH:32]=1.S(Cl)(Cl)(=O)=O.[Sn]>>[SH:13][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][CH2:31][CH3:32])=[O:11])=[C:2]([CH3:1])[CH:3]=1

Komponenten

Edukt 4

HCID 335O-Cresol

HCID 24648Sulfuryl chloride

HCID 5352426Tin atom

HCID 9803963GW 5015162×

Produkt 1

HCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetate

Versuchsvorschrift

As an alternative synthesis method of GW501516, it is disclosed, as illustrated in the following scheme (2), that the compound (13) of GW501516 can be prepared by introducing ethyl acetate group to o-cresol (14), reacting the resulted compound (15) with sulfonyl chloride, reducing the resulted compound (16) with tin (Sn) under acidic condition to form ethyl (4-mercapto-2-methyl phenoxy)acetate (17), reacting it with 5-chloromethyl-4-methyl-2-(4-trifluoromethyl phenyl)thiazole (11) together with an excessive cesium carbonate to obtain the ethyl ester intermediate (18) of GW501516, and deprotecting the ester group of the intermediate compound with 1N lithium hydroxide.

Aufarbeitung

customcan be prepared

Quellen und Nachweise

ORD-Eintrag: ord-3293be9e9c0b4cc88b6f07357881eafa
Quelldatensatz: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07982050B2

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