Boron trifluoride etherate → HCID 71078475, compound

HRID 2206786Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:4][C:5]([C:11]2(OC)[C@H:16]([OH:17])[C@@H:15]([OH:18])[C@H:14]([OH:19])[C@@H:13]([CH2:20][OH:21])[O:12]2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl.CC#N>[Br:1][C:2]1[C:3]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[CH:4][C:5]([C@H:11]2[C@H:16]([OH:17])[C@@H:15]([OH:18])[C@H:14]([OH:19])[C@@H:13]([CH2:20][OH:21])[O:12]2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of compound 15 (0.94 g, 1.85 mmol) in CH2Cl2/CH3CN (8.9 mL/8.9 mL) were added triethylsilane (0.59 mL, 3.7 mmol) and boron trifluoride diethyl etherate (0.46 mL, 3.7 mmol) at −60° C. under nitrogen atmosphere. The mixture was warmed up to −30° C. for 2 h. The reaction mixture was quenched with saturated NaHCO3 solution (15 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by prep HPLC (reverse phase) to provide the compound E001 (0.15 g, 0.306 mmol, 17%).

Workup

customThe reaction mixture was quenched with saturated NaHCO3 solution (15 mL)
extractionextracted with EtOAc (50 mL)
washThe organic layer was washed with brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by prep HPLC (reverse phase)
customto provide the compound E001 (0.15 g, 0.306 mmol, 17%)

Sources & evidence

ORD record: ord-575d1b8b49e4407aa52fff398fe3e721
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371303B2

Reaction notes

Loading…