Trifluoroacetic acid → HCID 69082386, compound

Participants

Reaction Steps

A solution of (3aR,5S,6S,7R,7aR)-5-((S)-1-fluoroethyl)-6,7-bis(4-methoxybenzyloxy)-N,N-dimethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine (240 mg, 0.48 mmol) in dichloromethane (20 mL) was treated with TFA (2 mL) for 1 h at room temperature. The reaction mixture was concentrated under reduced pressure to give a residue, which was purified by Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18, 19*50 mm 5 um; mobile phase, water with 0.03% NH4OH and CH3CN (10% CH3CN up to 45% in 10 min); Detector, UV 220 nm] to afford compound 51 (Example 9) as a white solid (30 mg, 24%). (ES, m/z): [M+H]+ 265.0; 1H NMR (300 MHz, D2O) δ 6.23-6.25 (d, J=6.0 Hz, 1H), 4.93-4.99 (m, 0.5H), 4.77-4.84 (m, 0.5H), 4.17 (t, J=6.0 Hz, 1H), 4.00 (t, J=6.0 Hz, 1H), 3.71-3.74 (m, 1H), 3.36-3.49 (m, 1H), 2.94 (s, 1H), 1.25-1.35 (dd, J=6.6 Hz, 6.3 Hz, 3H).

Provenance & Evidence