4-Methylmorpholine → HCID 131718973, compound

Participants

Reaction Conditions

Reaction Steps

Z-Lys(BOC) (0.75 g, 1.98 mmol), Pro-Trp-Tle-Leu-OEt (Seq ID No: 7), (1.0 g, 1.8 mmol) (prepared by catalytic hydrogenation of Z-Pro-Tle-Leu-OEt (Seq ID No: 7) over palladium on charcoal), and NMM (0.36 mL) is dissolved in 15 mL DMF, cooled to 0° C., and treated with TBTU (0.635 g, 1.98 mmol). The reaction is stirred at 0° C. for 1 hour then removed from the ice bath and stirred at room temperature for 3 hours. The mixture is poured into 150 mL of a saturated solution of sodium carbonate which is then extracted with two 150 mL portions of ethyl acetate. The combined organic extracts are washed with 150 mL of 1 M KHSO4, water and brine, and then dried over sodium sulfate. The solvents are removed under reduced pressure and the residue is chromatographed on silica gel. (2% MeOH in chloroform with 0.1% NH3) to give Z-Lys(BOC)-Pro-Trp-Tle-Leu-OEt (Seq ID No: 9) (1.34 g). FABMS M+1 818 (M-tBu)

Provenance & Evidence