Methanesulfonyl chloride → HCID 86611758, compound

Participants

Reaction Steps

A solution of N-{(S)-2-[(3R,4R)-4-(2,5-Dimethyl-benzoimidazol-1-yl)-3-hydroxy-piperidin-1-ylmethyl]-indan-5-yl}-isobutyramide; compound with trifluoro-acetic acid (235 mg; 0.51 mmol) and diisopropylethylamine (122 mL; 0.7 mmol) in CH2Cl2 was treated with methanesulfonyl chloride (47 mL; 0.6 mmol). The reaction mixture was stirred for 1 h and then poured into saturated NaHCO3. The aqueous phase was extracted three times with CH2Cl2 and the combined organic layers were dried over Na2SO4. Filtration and removal of volatiles under reduced pressure gave a brown solid from which the methanesulfonic acid 4-(2,5-dimethyl-benzoimidazol-1-yl)-1-((R)-5-isobutyrylamino-indan-2-ylmethyl)-piperidin-3-yl ester was isolated by flash chromatography (0-10% CH3OH in EtOAc) as a waxy solid (171 mg; 62%)

Provenance & Evidence