Boron Trichloride → HCID 71152501, compound

HRID 1481614Notes

Reaction equation

C([O:8][C@@H:9]1[C@@H:17]([C@:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:25](C)[C:26](=O)OC(C)(C)C)[S:14]2)[C@H:10]1[F:34])C1C=CC=CC=1.B(Cl)(Cl)Cl>>[F:34][C@@H:10]1[C@H:11]2[N:12]=[C:13]([NH:25][CH3:26])[S:14][C@H:15]2[O:16][C@H:17]([C@:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])[C@H:9]1[OH:8]

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 131736642HCID 131736642, compound

Product 1

HCID 71152501HCID 71152501, compound

Procedure

The above material, tert-butyl ((3aR,5S,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-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 (0.200 g, 0.394 mmol), was deprotected with BCl3 using the procedure described for Example 20. After purification on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:15), (3aR,5S,6R,7R,7aR)-7-fluoro-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 (0.114 g, 91%). 1H NMR (400 MHz, CD3OD) δ 6.29 (d, J=6.8 Hz, 1H), 5.05-4.93 (m, 1H), 4.55-4.51 (m, 1H), 4.15-4.08 (m, 1H), 3.73 (d, J=8.6 Hz, 1H), 2.85 (s, 3H), 1.34 (s, 3H); 13C NMR (100 MHz, CD3OD) δ 164.35 (d, J=2.7 Hz), 127.35 (q, J=284.3 Hz), 93.14 (d, J=175.8 Hz), 89.65, 75.73 (q, J=27.3 Hz), 73.40 (d, J=27.2 Hz), 72.90, 68.88 (d, J=25.6 Hz), 30.85, 16.75 (q, J=1.3 Hz); MS, (ES, m/z) [M+H]+ 318.1.

Workup

customAfter purification on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:15)

Sources & evidence

ORD record: ord-d186962ec4fb41d48903c362371927c1
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409924B2

Reaction notes

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