Boron Trichloride → HCID 71152223, compound

HRID 1481607Notes

Reaction equation

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

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 71152564HCID 71152564, compound

Product 1

HCID 71152223HCID 71152223, compound

Procedure

The material described above, 1-((3aR,5R,6S,7aR)-6-(benzyloxy)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)ethanol (0.180 g, 0.558 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, 1:12), (3aR,5R,6S,7aR)-5-((S)-1-hydroxyethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3 aH-pyrano[3,2-d]thiazol-6-ol was obtained as a white solid (0.105 g, 81%) and as a mixture of diastereomers.

Workup

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

Sources & evidence

ORD record: ord-9b252bc0703f40928a4890de467b63d4
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409924B2

Reaction notes

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