Triethylamine → HCID 86668863, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((3R)-3-(benzyloxycarbonyl)-1-hydroxycyclopentyl)acetic acid (from step B, 130 mg, 0.467 mmol) in a mixture of toluene (2 mL) and tetrahydrofuran (1.0 mL) was added triethylamine (0.098 mL, 0.701 mmol) and diphenylphosphoryl azide (154 mg, 0.561 mmol) at room temperature. The resulting mixture was heated to 80° C. for 45 min. The reaction mixture was concentrated and the residue was subjected to preparative HPLC (Shimadzu VP-ODS 20×100 mm, 8 min. gradient, Solvent A: 10% MeOH, 90% H2O, 0.1% TFA; Solvent B: 90% MeOH, 10% H2O, 0.1% TFA). The fractions corresponding to the individual diasteromers were collected, concentrated, freeze dried and taken forward individually. Isomer 1: 20 mg, 0.073 mmol, 15.5% yield, MS (ESI+) m/z 276 (M+H)+; Isomer 2: 20 mg, 0.073 mmol, 15.5% yield, MS (ESI+) m/z 276 (M+H)+

Provenance & Evidence