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

HRID 1014070

Reaction equation

HRID 1014070 reaction equation
[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

Participants

5

Reactant 4

HCID 335O-CresolHCID 24648Sulfuryl chlorideHCID 5352426Tin atomHCID 9803963GW 5015162×

Product 1

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

Procedure

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.

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-3293be9e9c0b4cc88b6f07357881eafa
Source dataset
uspto-grants-2011_07
Patent number
US07982050B2

Linked notes

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