Hydrochloric Acid → HCID 14308498, compound

Participants

Reaction Conditions

Reaction Steps

8.3 g of Boc-Pro (38.45 mmol) were dissolved in 50 ml of CH2Cl2, cooled down to +5° C., and 38.45 mmol (5.38 ml) of TEA were added. The reaction mixture was cooled down to −25÷−30° C. At this temperature, 38.45 mmol (4.84 ml) of isobutyl chloroformate were added using a pipette. The reaction mixture temperature was kept in the range of −18±−20° C. for 20 minutes. Simultaneously, a solution of 5.9 g (42.3 mmol) of 1.1-fold excess of HCl.H-Gly-OEt in 75 ml of chloroform, containing 5.92 ml of TEA. The solution was cooled down to −25° C. and, after formation of mixed anhydride in the first flask, its contents were poured to the ether solution right away. The reaction mixture was incubated for 1 hour at −10° C. and then stirred for 12 hours at 4° C. on a magnetic stirrer. The reaction mixture was evaporated and 250 ml of ethyl acetate were added to it; the ethyl acetate solution was washed 3 times with 25 ml of 0.1N HCl, 3 times with 25 ml H2O, and once with saturated solution of NaCl. The organic layer was dried over MgSO4, filtered and evaporated. The residue was dried under vacuum over P2O5/KOH and paraffin.

Provenance & Evidence