Boron Trichloride → HCID 71152292, compound

HRID 1481609Notes

Reaction equation

C([O:8][C@@H:9]1[C@@H:17]([C@@H:18]([OH:23])[C:19]([F:22])([F:21])[F:20])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:24](C)[C:25](=O)OC(C)(C)C)[S:14]2)[CH2:10]1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[CH3:25][NH:24][C:13]1[S:14][C@H:15]2[O:16][C@H:17]([C@@H:18]([OH:23])[C:19]([F:22])([F:20])[F:21])[C@@H:9]([OH:8])[CH2:10][C@H:11]2[N:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To tert-butyl ((3aR,5R,6S,7aR)-6-(benzyloxy)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.052 g, 0.11 mmol) and PMB (0.10 g, 0.67 mmol) in anhydrous DCM (5 mL) at −78° C. under N2, was added BCl3 (1.0 M in DCM, 0.60 mL, 0.60 mmol). The mixture was stirred for ˜3 h while the temperature of the cooling bath warmed to 0° C. The reaction mixture was cooled at −78° C., quenched with mixed MeOH/DCM, and then concentrated to dryness. The residue was purified on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:12), affording (3aR,5S,6S,7aR)-2-(methylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-6-ol as a white solid (0.023 g, 74%). 1H NMR (400 MHz, CD3OD) δ 6.21 (d, J=6.4 Hz, 1H), 4.29-4.24 (m, 1H), 4.21-4.15 (m, 1H), 4.01-3.96 (m, 1H), 3.70 (d, J=8.8 Hz, 1H), 2.83 (s, 3H), 2.22-2.16 (m, 1H), 2.08-2.01 (m, 1H); 13C NMR (100 MHz, CD3OD) δ 163.69, 126.47 (q, J=281.2 Hz), 91.73, 73.5 (br.), 69.62 (q, J=30.1 Hz), 69.34, 64.60, 35.16, 30.60; MS, (ES, m/z) [M+H]+ 287.1.

Workup

temperatureThe reaction mixture was cooled at −78° C.
customquenched with mixed MeOH/DCM
concentrationconcentrated to dryness
customThe residue was purified on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:12)

Sources & evidence

ORD record: ord-7ba14647789d4f7fa213fb772e16cc47
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409924B2

Reaction notes

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