1-Methylimidazole → HCID 86652494, compound

Participants

Reaction Conditions

Reaction Steps

Compound 1 (100 mg) was dissolved in dry THF/pyridine together with (2S)-benzyl 2-(chloro(phenoxy)phosphorylamino)propanoate (279 mg, 2.0 eq). The mixture was cooled to −78° C. N-methylimidazole (NMI) (259 mg, 8 eq) was added and this mixture was stirred for 15 minutes at −78° C. and then stirred at RT overnight. The resulting mixture was evaporated to dryness. 10 mL CH2Cl2 added and the residue washed with 10 mL 0.5N HCl. The organic layer was separated and washed with 10 mL water, dried on Na2SO4, filtered and evaporated. The compound was purified by silica gel chromatography using CH2Cl2 to CH2Cl2/MeOH 9-1 as the eluent. (Rf=0.2 in this eluent). A yellow solid was obtained, which was repurified using column chromatography using EtOAc to EtOAc/MeOH 8-2 as the eluent. After evaporation and drying overnight in vacuo, 80 mg (33.4%) of 2a was obtained (mixture of diastereomers). LC-MS: Rt: 3.37 min m/z: 569 (M−H)−. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.31-0.41 (m, 1H), 0.43-0.58 (m, 2H), 0.95-1.06 (m, 1H), 1.20-1.31 (m, 3H), 3.82-4.01 (m, 3H), 4.09-4.23 (m, 1H), 4.23-4.36 (m, 1H), 4.98-5.15 (m, 2H), 5.29-5.39 (m, 1H), 5.70 (d, J=7.43 Hz, 1H), 6.07 (s, 1H), 6.13 (dd, J=12.81, 10.47 Hz, 1H), 7.08-7.25 (m, 6H), 7.29-7.39 (m, 6H), 7.54 (d, 1H).

Provenance & Evidence