HCID 68491265, compound → HCID 9925373, compound

HRID 1826199Notes

Reaction equation

HRID 1826199 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:25]2[CH2:29][C@H:28]([C:30]([NH2:32])=[O:31])[O:27][C:26]2=[O:33])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:24])[CH2:15][O:16]CC2C=CC=CC=2)[CH2:10][CH2:9]1.[H][H]>CO.CCO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:25]2[CH2:29][C@H:28]([C:30]([NH2:32])=[O:31])[O:27][C:26]2=[O:33])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:24])[CH2:15][OH:16])[CH2:12][CH2:13]1

Participants

6

Reactant 2

HCID 68491265HCID 68491265, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9925373HCID 9925373, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of (5R)-3-[3-fluoro-4-[4-[(phenylmethoxy)acetyl]-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinecarboxamide (Step 2, 260 mg, 0.570 mmol) and 10% palladium-on-carbon (61 mg, 0.0570 mmol) in a mixture of methanol (5 mL) and EtOH (23 mL) was shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 22 hours. The catalyst was then removed by filtration through a pad of Celite, rinsing with tetrahydrofuran (200 mL), and the filtrate was concentrated under reduced pressure and triturated with methanol/diethyl ether. Filtration then provided the title compound, mp 232-235° C. (dec.); MS (ESI+) for C16H19FN4O5 m/z 367 (M+H)+; [α]25D=−20 (c 0.98, DMSO).

Workup

  1. customThe catalyst was then removed by filtration through a pad of Celite
  2. washrinsing with tetrahydrofuran (200 mL)
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customtriturated with methanol/diethyl ether
  5. filtrationFiltration

Sources & evidence

ORD record
ord-4ff70083882b4a9d9bb1c2ee1856c733
Source dataset
uspto-grants-2006_05
Patent number
US07049443B2

Reaction notes

Loading…