Boron trifluoride etherate → N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1699659Notes

Reaction equation

HRID 1699659 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:19]2[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]2=[O:29])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[N:10](CC=C)[CH2:9]1.B(F)(F)F.CCOCC>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[C:4]([N:19]2[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]2=[O:29])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:14])(=[O:15])[NH:10][CH2:9]1

Participants

5

Reactant 2

HCID 8000Boron trifluoride etherateHCID 9910287N-[[(5S)-3-[3-Fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 9908135N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[[(5S)-3-[3-Fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (350 mg, 0.82 mmol), 10% palladium on carbon (500 mg), boron trifluoride etherate (179 mg, 1.26 mmol) and absolute ethanol (8 ml) are heated under reflux for 5 hr. Upon cooling the suspension is filtered and evaporated. Chromatography over silica gel (55 g) eluting with 2-6% methanol-chloroform affords the title compound as a foam (186 mg, 59%). HRMS(FAB): calcd for m+H=386.1186; Found: 386.1194.

Workup

  1. temperatureunder reflux for 5 hr
  2. temperatureUpon cooling the suspension
  3. filtrationis filtered
  4. customevaporated
  5. washChromatography over silica gel (55 g) eluting with 2-6% methanol-chloroform

Sources & evidence

ORD record
ord-04bf692e21eb4f9fb47f22f20edbbc0c
Source dataset
uspto-grants-2002_02
Patent number
US06348459B1

Reaction notes

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