4-Chlorobenzoic Acid → HCID 67774379, compound

Participants

Reaction Steps

To 4-chlorobenzoic acid (65.7 mg, 0.42 mmol) and DIPEA (0.365 mL, 2.10 mmol) in DCM (0.7 mL) was TBTU (148 mg, 0.46 mmol) added 1-((2R,3R)-3-Methoxy-2-(methylamino)butyl)azetidin-3-ol (Compound B2.2) (79 mg, 0.42 mmol) in DCM (0.7 mL) was added and the resultant mixture stirred at rt for 2 h. NaHCO3 was added and the stirring continued for 30 min. The layers were separated and the organic phase concentrated under reduced pressure. The residue was dissolved in THF/MeOH/water (3:1:1) and a small amount of NaOH (3.8M) was added. The resultant mixture was stirred for 30 min. The mixture was diluted with water and the organic solvent was removed. The water layer was extracted with DCM. The combined organic layers were filtered through a phase separator and concentrated. The residue was purified by preparative HPLC to give the title compound (39 mg, 28%). Mixture of rotamers: 1H NMR (600 MHz, DMSO-d6) δ 0.92, 1.08, 2.34-2.40, 2.52-2.59, 2.63, 2.69, 2.70-2.76, 2.77, 3.18-3.23, 3.34-3.39, 3.44-3.48, 3.48-3.54, 4.04-4.10, 4.11-4.16, 4.40, 5.16-5.24, 7.31, 7.40, 7.43-7.50. Total of protons in spectrum: 22. Ratio major:minor:3:2. HRMS (M+H)+: calculated 327.1475. found 327.1476.

Provenance & Evidence