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0 °C

Methyl 4-(5-chloro-2-(3-(3,3-diphenylpropyl)-3-isopropylureido)thiazol-4-yl)benzoate 175 (0.424 g, 0.774 mmol) was dissolved in THF (5 mL) and cooled to 0° C. To this solution, lithium aluminium hydride (2M solution in THF, 0.77 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 1 h, quenched with Rochelle's salt solution and then extracted with ethyl acetate. Organics were concentrated and purified by column chromatography on silica using 1:1 EtOAc:Hexane. Product 176 was obtained as a solid (0.38 g, 95%). Mass spectrum: calculated for C29H30ClN3O2S 519.2; found 520.2 (M+H).

1. customquenched with Rochelle's salt solution
2. extractionextracted with ethyl acetate
3. concentrationOrganics were concentrated
4. custompurified by column chromatography on silica using 1:1 EtOAc