Boron trifluoride etherate → HCID 86753534, compound

HRID 342291Notes

Reaction equation

[Si]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[N:13]([C@@H:25]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C:26]([CH3:28])=[CH2:27])[C:12]1=[O:42])[CH3:10])(C(C)(C)C)(C)C.B(F)(F)F.CCOCC>C(#N)C.C(OCC)(=O)C>[OH:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[N:13]([C:25]([C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)=[O:30])=[C:26]([CH3:28])[CH3:27])[C:12]1=[O:42])[CH3:10]

Participants

Conditions

Temperature: -15 °C

Procedure

64 mg (0.104 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-1-[(R)-2-methyl-1-(p-nitrobenzyloxycarbonyl)prop-2-enyl]-4-[(phenylthio)-carbonylmethyl]-2-azetidinone were dissolved in 1.5 ml of acetonitrile. To the solution were added, with stirring at -15° C., 15 mg (0.106 mmole) of boron trifluoride etherate. After 30 minutes, the reaction mixture was diluted with ethyl acetate and washed with a dilute aqueous solution of sodium bicarbonate. The solvent was distilled off under reduced pressure and the resulting residue was subjected to thin layer chromatography using silica gel, developed with a 2:3 by volume mixture of benzene and ethyl acetate, to afford 48 mg (yield 92%) of the title product.

Workup

additionTo the solution were added
washwashed with a dilute aqueous solution of sodium bicarbonate
distillationThe solvent was distilled off under reduced pressure
additiondeveloped with a 2:3 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record: ord-f5b52d7eef574ac5b1fbf503d2465174
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856556

Reaction notes

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