Sodium Azide → HCID 86594308, compound

Participants

Reaction Conditions

Reaction Steps

A solution of compound 90A (400 mg, 1.18 mmol) and sodium azide (309 mg, 4.75 mmol) in anhydrous DMF (3.2 mL) was placed in a pre-heated bath (75° C.) and stirred at 75° C. for 3 h. The solution was cooled, quenched with H2O (6.0 mL) and extracted with EtOAc (2×80 mL). The organic phase was washed with H2O (6.0 mL), brine (6.0 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The syrup was chromatographed (silica gel; CH2Cl2/CH3OH gradient) to yield the title compound (339.3 mg, 90.8%) as a white solid foam from CH2Cl2/Hexane. HPLC: 97.7% at 2.22 min (retention time) (Conditions: YMC S-5 C-18 (4.6×50 mm), eluting with 0-100% B, 4 min gradient. (A=90% H2O—10% CH3CN—0.1% TFA and B=10% H2O—90% CH3CN—0.1% TFA); Flow rate at 4 mL/min. UV detection at 220 nm. MS (ES+): m/z 317 [M+H]+.

Provenance & Evidence