Boron trifluoride etherate → HCID 67791552, compound

HRID 1090531Notes

Reaction equation

[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1/[CH:12]=[C:13](\[CH3:32])/[C:14](=[O:31])[CH2:15][CH:16]1[NH:19][C:18](=[O:20])[CH:17]1[C@H:21]([O:23][Si](C(C)(C)C)(C)C)[CH3:22])=[O:6])[CH:2]=[CH2:3].B(F)(F)F.CCOCC.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(#N)C.O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1/[CH:12]=[C:13](\[CH3:32])/[C:14](=[O:31])[CH2:15][C@H:16]1[NH:19][C:18](=[O:20])[C@@H:17]1[C@H:21]([OH:23])[CH3:22])=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3S,4R)-4-[(E)-4-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]-3[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (33.90 g) in acetonitrile (68 ml) was added boron trifluoride etherate (19.74 ml) at 5°-10° C. After stirring at 0° C. for 30 minutes, the reaction mixture was taken up into a mixture of ethyl acetate (170 ml), water (140 ml) and sodium bicarbonate (13.48 g). After stirring for 30 minutes, the organic layer was separated. The aqueous layer was extracted with ethyl acetate (70 ml). The combined organic portion was washed with brine (100 ml) and dried over magnesium sulfate. The solvent was removed in vacuo to give (3S,4R)-4-[(E)-4-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]3-[(1R)-1-hydroxyethyl]-2-oxoazetidine.

Workup

stirringAfter stirring for 30 minutes
customthe organic layer was separated
extractionThe aqueous layer was extracted with ethyl acetate (70 ml)
washThe combined organic portion was washed with brine (100 ml)
dry with materialdried over magnesium sulfate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-5ba8f26f0e814cc7b5ec8abf80b5d9f8
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05081237

Reaction notes

Loading…