Methanesulfonyl chloride → HCID 86599409, compound

Participants

Reaction Steps

To a solution of (5S,7R)-5-(4-bromobenzyl)-3-(3,5-dichloro-phenyl)-7-hydroxy-1,3-diazabicyclo[3.3.0]octane-2,4-dione (0.81 g) in CH2Cl2 (5 mL) and DIEA (0.50 mL) at 0° C. was added methanesulfonyl chloride (0.19 mL). After 1 hour at 0° C., the mixture was diluted with CH2Cl2, washed with satd. NaHCO3 and brine, dried (Na2SO4) and concentrated to give (5S, 7R)-5-(4-bromobenzyl)-3-(3,5-dichlorophenyl)-7-methylsulfonyloxy-1,3-diazabicyclo[3.3.0]octane-2,4-dione. MS (m/z) 494 (MH+). (2) To a solution of the compound obtained above in DMF (4 mL) at 75° C. was added sodium azide (0.54 g). After heating for 2 hours the mixture was diluted with Et2O and water. The organic solution was collected, washed with water and brine, dried (Na2SO4), filtered and concentrated. Purification by chromatography (silica gel: 2% methanol/CH2Cl2, Chromatotron) afforded the titled compound (0.82 g). MS (m/z) 494 (MH+), mp 58.9° C.

Provenance & Evidence