Water → HCID 59369849, compound

Participants

Reaction Steps

To a solution of racemic 7-2 (9.6 g, 38.8 mmol) in dichloromethane (190 mL) at 0° C. was added triethylamine (7.86 g, 78.0 mmol) followed by methanesulfonyl chloride (6.67 g, 58.2 mmol) and the reaction mixture was slowly warmed to ambient temperature over 24 h. The mixture was then quenched with water and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to an oil. The residue was dissolved in dimethylformamide (100 mL) and to this mixture was added sodium azide (10.1 g, 155 mmol). The reaction mixture was heated to 90° C. for 15 h. The reaction was cooled and partition between EtOAc (300 mL) and water (100 mL). The organic phase was washed with water (3×100 mL), and the organic phase was dried over MgSO4 and concentrated to an oil. The oil was dissolved in THF (370 mL) and to this was added polymer-bound triphenylphosphine (18.4 g, 40.4 mmol, 2.2 mmol/g loading) and water (6.6 g, 367 mmol). The reaction was heated to 50° C. for 2 h and the reaction was complete. The reaction was cooled to ambient temperature dried over MgSO4 and concentrated to yield >80% pure product as an oil which was used as is in the next reaction. ESI+ MS: [M+H]+ 247.4.

Provenance & Evidence