Boron Trichloride → HCID 71152257, compound

HRID 1481616Notes

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]([CH2:33][CH3:34])C(=O)OC(C)(C)C)[S:14]2)[C@H:10]1[F:35])C1C=CC=CC=1.B(Cl)(Cl)Cl>>[CH2:33]([NH:25][C:13]1[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]([OH:8])[C@H:10]([F:35])[C@H:11]2[N:12]=1)[CH3:34]

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 131736644HCID 131736644, compound

Product 1

HCID 71152257HCID 71152257, 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)(ethyl)carbamate (0.100 g, 0.191 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, 1:17), (3aR,5S,6R,7R,7aR)-2-(ethylamino)-7-fluoro-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 (0.053 g, 84%). 1H NMR (400 MHz, CD3OD) δ 6.26 (d, J=6.8 Hz, 1H), 5.04-4.92 (m, 1H), 4.54-4.50 (m, 1H), 4.15-4.07 (m, 1H), 3.73 (d, J=8.6 Hz, 1H), 3.34-3.21 (m, 2H), 1.33 (s, 3H), 1.17 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CD3OD) δ 163.47 (d, J=2.2 Hz), 127.40 (q, J=284.2 Hz), 93.11 (d, J=175.6 Hz), 89.36, 75.75 (q, J=27.3 Hz), 73.50 (d, J=27.2 Hz), 72.90, 68.94 (d, J=25.7 Hz), 39.95, 16.72 (q, J=1.5 Hz), 14.98; MS, (ES, m/z) [M+H]+ 333.1.

Workup

customAfter purification on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:17)

Sources & evidence

ORD record: ord-1d9516ff999944509d0205617f1a2cb4
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409924B2

Reaction notes

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