Boron trifluoride etherate → HCID 86753540, compound

HRID 342295Notes

Reaction equation

HRID 342295 reaction equation
[Si]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:18][C@H:19]2[CH2:23][CH2:22][N:21]([C:24](=[N:26][C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=3)=[O:28])[CH3:25])[CH2:20]2)=[O:17])[N:13]([C:40]([C:44]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][CH:49]=2)=[O:45])=[C:41]([CH3:43])[CH3:42])[C:12]1=[O:57])[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@H:19]2[CH2:23][CH2:22][N:21]([C:24](=[N:26][C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=3)=[O:28])[CH3:25])[CH2:20]2)=[O:17])[N:13]([C:40]([C:44]([O:46][CH2:47][C:48]2[CH:49]=[CH:50][C:51]([N+:54]([O-:56])=[O:55])=[CH:52][CH:53]=2)=[O:45])=[C:41]([CH3:42])[CH3:43])[C:12]1=[O:57])[CH3:10]

Participants

5

Reactant 2

HCID 8000Boron trifluoride etherateHCID 88672372HCID 88672372, compound

Product 1

HCID 86753540HCID 86753540, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

511 mg (0.62 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-([(S)-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidin-3-ylthio]carbonylmethyl)-1 -[2-methyl-1-(p-nitrobenzyloxycarbonyl)prop-1-enyl]-2-azetidinone were dissolved in 20 ml of acetonitrile. To this solution were added 176 mg (1.24 mmole) of boron trifluoride etherate, with stirring and ice-cooling. The reaction mixture was then left to stand at room temperature for 2.5 hours, after which it was diluted with ethyl acetate, washed with an aqueous solution of sodium bicarbonate and dried. The solvent was distilled off, to afford 462 mg of the title product.

Workup

  1. temperatureice-cooling
  2. waitThe reaction mixture was then left
  3. washwashed with an aqueous solution of sodium bicarbonate
  4. customdried
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-dbc18839461645329b35292524a9633f
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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