Boron trifluoride etherate → HCID 86701295, compound

HRID 2282997Notes

Reaction equation

[CH3:1][C:2](=[CH2:17])[CH2:3][O:4][C@H:5]([C@@H:8]([O:12][CH2:13][C:14]([CH3:16])=[CH2:15])[C@@H:9]([OH:11])[CH3:10])[CH2:6][OH:7].[N@:18]1([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:20][CH:19]1[C:21]([O:23][CH3:24])=[O:22].B(F)(F)F.CCOCC>C(Cl)(Cl)Cl>[CH2:28]([O:27][C:25]([NH:18][C@@H:19]([CH2:20][O:7][CH2:6][C@H:5]([O:4][CH2:3][C:2]([CH3:1])=[CH2:17])[C@@H:8]([O:12][CH2:13][C:14]([CH3:16])=[CH2:15])[C@@H:9]([OH:11])[CH3:10])[C:21]([O:23][CH3:24])=[O:22])=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1.[CH2:28]([O:27][C:25]([NH:18][C@@H:19]([CH2:20][O:11][C@H:9]([C@H:8]([O:12][CH2:13][C:14]([CH3:16])=[CH2:15])[C@@H:5]([O:4][CH2:3][C:2]([CH3:1])=[CH2:17])[CH2:6][OH:7])[CH3:10])[C:21]([O:23][CH3:24])=[O:22])=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2S,3S,4S)-2,3-bis(2-methylallyloxy)pentane-1,4-diol (920 milligrams (mg), 3.77 mmol) and (S)-1-benzyl 2-methyl aziridine-1,2-dicarboxylate (0.739 mL, 3.74 mmol) in anhydrous chloroform (CHCl3; 5 mL) was added BF3-Et2O (26 microliters (μL) 0.55 mmol) at 0° C. and the solution was stirred at 0° C. for 3 h. The crude reaction mixture was concentrated and purified by flash chromatography (SiO2) to furnish (S)-methyl 2-(benzyloxycarbonylamino)-3-((2S,3S,4S)-4-hydroxy-2,3-bis(2-methylallyloxy)-pentyloxy)-propanoate as a colorless oil (620 mg, 35%) and (S)-methyl 2-(benzyloxycarbonylamino)-3-((2S,3S,4S)-5-hydroxy-3,4-bis(2-methylallyloxy)pentan-2-yloxy)propanoate as a colorless oil (300 mg, 17%).

Workup

customThe crude reaction mixture
concentrationwas concentrated
custompurified by flash chromatography (SiO2)

Sources & evidence

ORD record: ord-820c6c81d4954a518cba2316ebb81055
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09144239B2

Reaction notes

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