Boron Trichloride → HCID 71152456, compound

HRID 1481620Notes

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)[CH2:10]1)C1C=CC=CC=1.B(Cl)(Cl)Cl>>[CH3:26][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:20])([F:21])[F:22])[C@@H:9]([OH:8])[CH2:10][C@H:11]2[N:12]=1

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 123334676HCID 123334676, compound

Product 1

HCID 71152456HCID 71152456, compound

Procedure

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.

Workup

customAfter purification on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:12)

Sources & evidence

ORD record: ord-f0007194b9fa4c6d8f2b511887d9707f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409924B2

Reaction notes

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