4-Methylmorpholine → HCID 67773057, compound

Participants

Reaction Conditions

Reaction Steps

(S)-2-(Tert-butoxycarbonylamino)-3-methylbutanoic acid (7.00 g, 30.3 mmol) and TBTU (9.72 g, 30.27 mmol) was mixed in DMF (70 mL). The mixture was cooled to 0° C. and NMM (3.99 mL, 36.3 mmol) was added. After 10 min was pyrrolidine (3.00 mL, 36.32 mmol) added. The resultant mixture was stirred at 0° C. for 30 min. and at rt over night. The mixture was concentrated and the residue dissolved in DCM (250 mL). The organic phase was washed with NaHCO3 (saturated, 2×200 mL) and brine (200 mL), filtered through a phase separator and concentrated under reduced pressure. The residue was purified via Biotage (gradient; DCM/iso-propanol, 99:1 to 90:10, KP-SIL 340 g column). The solvent was removed under reduced pressure to give the title compound (6.4 g, 74%). 1H NMR (400 MHz, CDCl3) δ 0.99, 1.43, 1.80-2.01, 3.31-3.45, 3.47-3.59, 3.67-3.79, 4.29, 5.28. Total no of protons: 27. LCMS (M+H)+: 285.

Provenance & Evidence