p-Toluenesulfonic acid → HCID 68556594, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of [(3R*,4S*,5S*)-5-(4-benzyloxycarbonylamino-3-fluoro-benzyl)-4-hydroxy-tetrahydro-thiopyran-3-yl]-carbamic acid tert-butyl ester (50.5 g, 102.9 mmol) and acetone dimethylketal (263 mL, 2.06 mol) in CH2Cl2 (500 mL) was added p-TsOH (200 mg, 1 mmol) at 0-5° C. and the reaction mixture was stirred for 4 h at 25° C. The reaction mixture was washed with saturated NaHCO3 solution and water, dried over MgSO4, filtered and evaporated to dryness. The title compound obtained as a yellow oil was used as such in the next step: TLC (toluene-EtOAc 3:1) Rf=0.40; HPLC RtA=2.80 min; ESIMS [M−H]−=529; 1H NMR (400 MHz, CDCl3): δ 7.99 (m, 1H), 7.38 (m, 5H), 6.92 (m, 2H), 6.84 (s, 1H), 5.21 (s, 2H), 3.3-3.6 (m, 2H), 3.03 (m, 2H), 2.52 (m, 2H), 2.38 (dt, 1H), 2.34 (t, 1H), 2.20 (m, 1H), 1.58 (s, 3H), 1.52 (s, 3H), 1.43 (s, 9H).

Provenance & Evidence