HCID 9879568, compound → HCID 9879646, compound

HRID 1991241Notes

Reaction equation

HRID 1991241 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([C:18]([NH2:20])=[O:19])[O:15][C:14]3=[O:21])=[CH:9][C:8]=2[F:22])[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([C:18]([NH2:20])=[O:19])[O:15][C:14]3=[O:21])=[CH:9][C:8]=2[F:22])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 9879568HCID 9879568, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9879646HCID 9879646, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (5R)-(−)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide (EXAMPLE 9, Step 2, 200 mg, 0.653 mmol) and 10% palladium-on-carbon (139 mg, 0.131 mmol) in methanol (26 mL) is shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 5 h. The catalyst is then removed by filtration through a pad of Celite, and the filtrate is concentrated under reduced pressure and chromatographed on a Flash 40S 40 g silica gel (32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (2/98-3/97). Pooling and concentration of those fractions with an Rf=0.37 by TLC (methanol/chloroform, 2×5/95) gives the title compound, mp 153-156° C.; MS (ESI−) for C15H17N2O4F m/z 307 (M−H); [α]25D=−21 (c 0.87, DMSO).

Workup

  1. customThe catalyst is then removed by filtration through a pad of Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customchromatographed on a Flash 40S 40 g silica gel (32-63 μm) cartridge
  4. washeluting with a gradient of methanol/methylene chloride (2/98-3/97)

Sources & evidence

ORD record
ord-f865e1c65b324eacae527e7976a4dc29
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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