Methanol → H-Orn(Z)-ome hcl

Participants

Reaction Steps

To a solution of H-Orn(Z)—OH (1.00 μg, 3.76 mmol) in anhydrous MeOH (25 mL) at 0° C. was slowly added thionyl chloride (1.37 mL, 2.24 g, 18.8 mmol) as to maintain the internal reaction temperature below 10° C. After the addition was complete, the cold bath was removed, and stirring was continued for at rt 18 hours. The reaction was then concentrated under reduced pressure to afford a yellowish solid. Recrystallization with MeOH:EtOAc (1:6) afforded the desired product xliv as a white solid (600 mg, 0.190 mmol). The filtrate and EtOAc washings were cooled for 48 h at −20° C. to provide additional product xliv (177 mg, 0.56 1 mmol). The two batches (total: 777 mg, 2.46 mmol, 65%) were combined for further use.

Provenance & Evidence