5-Aminopentan-1-ol → HCID 68292892, compound

Participants

Reaction Steps

To a round bottom flask was added (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-methyl-3-(tritylthio)butanoic acid (400 mg, 0.652 mmol), HOBT (120 mg, 0.782 mmol), Hunig's Base (0.137 mL, 0.782 mmol), DMF (1 mL) and DCM (5 mL). The reaction was stirred at rt for 1 hr. Then 5-aminopentan-1-ol (67.2 mg, 0.652 mmol) was added to the reaction and the reaction was stirred at rt overnight. The reaction was diluted with EtOAc (50 mL) and washed with water (4×15 mL) and saturated aqueous NaCl (15 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give (R)-(9H-fluoren-9-yl)methyl 1-(5-hydroxypentylamino)-3-methyl-1-oxo-3-(tritylthio)butan-2-ylcarbamate (300 mg, 0.429 mmol, 65.9% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 7.76 (d, J=7.70 Hz, 2H), 7.69-7.50 (m, 8H), 7.39 (t, J=7.42 Hz, 2H), 7.33-7.15 (m, 11H), 5.74-5.41 (m, 2H), 4.45-4.11 (m, 3H), 3.67-3.39 (m, 2H), 3.35-3.07 (m, 2H), 1.56-1.41 (m, 4H), 1.42-1.31 (m, 2H), 1.33-1.24 (m, 2H), 1.18 (br. s., 3H), 1.11 (s, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 144.86, 141.28, 129.96, 127.86, 127.69, 127.07, 126.76, 125.11, 119.95, 68.35, 62.48, 53.38, 47.11, 39.35, 32.11, 29.01, 26.43, 22.93, 22.69, 14.09.

Provenance & Evidence