Boron Trichloride → HCID 71152517, compound

HRID 1481613Notes

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 131736641HCID 131736641, compound

Product 1

HCID 71152517HCID 71152517, compound

Procedure

The above material, tert-butyl ((3aR,5S,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3 aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.130 g, 0.256 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-((S)-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 (0.073 g, 90%). 1H NMR (400 MHz, CD3OD) δ 6.32 (d, J=6.8 Hz, 1H), 5.04-4.91 (m, 1H), 4.55-4.50 (m, 1H), 4.20-4.13 (m, 1H), 3.61 (d, J=8.5 Hz, 1H), 2.86 (s, 3H), 1.36 (s, 3H); 13C NMR (100 MHz, CD3OD) δ 164.36 (d, J=2.5 Hz), 127.43 (q, J=285.3 Hz), 93.67 (d, J=177.4 Hz), 89.21, 75.77 (q, J=27.0 Hz), 74.71 (d, J=1.4 Hz), 73.70 (d, J=26.7 Hz), 68.14 (d, J=25.0 Hz), 30.90, 18.90 (q, J=2.1 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-07868adcac1f44708bcc5bdc2f599a65
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409924B2

Reaction notes

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