2-Methylbenzenesulfonic acid hydrate → HCID 66861734, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (2S,3R)-4-(N-(4-cyanobenzyl)-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (921 mg, 1.68 mmol) was dissolved in EtOH (10 mL) and treated with toluenesulfonic acid monohydrate (337 mg, 1.77 mmol, 1.05 equiv). The mixture was allowed to stir at 65° C. for 40 min. LC-MS analysis showed that the starting material had been consumed and converted to the desired product. The solvent was removed and the residue was dissolved in CH2Cl2 (20 mL). The solution was treated with 1.0 M aq NaOH (20 mL) and the biphasic mixture was stirred for 0.5 h. The mixture was transferred to a separatory funnel and the layers were separated. The organic layer was dried over Na2SO4, filtered and evaporated to afford (2R,3S)-3-amino-1-(N-(4-cyanobenzyl)-N-(2-(trimethylsilyl)-ethoxycarbonyl)amino)-4-cyclohexylbutan-2-ol.

Provenance & Evidence