(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → HCID 86622354, compound

Participants

Reaction Conditions

Reaction Steps

Step AS (5). A mixture of 2-allyloxy-5-methoxybenzylamine (375 mg, 1.94 mmol), (2S,3S)-1,2-epoxy-3-(BOC-amino)-4-phenylbutane (818 mg, 3.1 mmol), and lithium perchlorate (514 mg, 4.85 mmol) in acetonitrile (6 mL) was stirred at 60° C. for 2.5 h. The reaction was concentrated and the residue was purified by silica gel chromatography, eluting with a mixture of 5% 2N ammonia in methanol and 95% EtOAc to yield 0.8 g of tert-butyl (2S,3R)-4-(2-(allyloxy)-5-methoxybenzylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate. The BOC-protected amine was dissolved in 10 mL 10% TFA/DCM and stirred at rt for 3 h. The reaction was concentrated under vacuum and the residue purified by reverse phase prep-HPLC to yield the titled compound as the ditrifluoroacetic acid salt (440 mg, 39%). LC-MS (M+H)+=357; 1H NMR (400 MHz, CD3OD) δ 7.30 (m, 5H) 7.00 (m, 3H) 6.10 (m, 1H) 5.40 (m, 1H) 5.30 (m, 1H) 4.61 (m, 2H) 4.22 (m, 3H) 3.76 (s, 3H) 3.66 (m, 1H) 3.18 (m, 1H) 2.90 (m, 3H).

Provenance & Evidence