Boron Trichloride → HCID 71152456, compound

Participants

Reaction Steps

The protected material, tert-butyl ((3aR,5S,6S,7aR)-6-(benzyloxy)-5-((R)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.160 g, 0.326 mmol), was deprotected using BCl3, as described for Example 20. After purification on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:12), (3aR,5S,6S,7aR)-2-(methylamino)-5-((R)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-6-ol was obtained as a white solid (0.072 g, 73%). 1H NMR (400 MHz, CD3OD) δ 6.18 (d, J=6.8 Hz, 1H), 4.44-4.41 (m, 1H), 4.19-4.15 (m, 1H), 3.67 (d, J=7.4 Hz, 1H), 2.85 (s, 3H), 2.29-2.24 (m, 1H), 2.09-2.03 (m, 1H), 1.31 (s, 3H); 13C NMR (100 MHz, CD3OD) δ 164.14, 127.51 (q, J=284.3 Hz), 91.42, 75.71 (q, J=27.0 Hz), 75.53, 70.18, 66.58, 33.47, 30.89, 16.96 (q, J=1.5 Hz); MS, (ES, m/z) [M+H]+ 301.1.

Provenance & Evidence