HCID 86590829, compound → HCID 10125766, compound

HRID 1826193Notes

Reaction equation

HRID 1826193 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([C:19]([NH:21][O:22]CC3C=CC=CC=3)=[O:20])[O:16][C:15]2=[O:30])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([C:19]([NH:21][OH:22])=[O:20])[O:16][C:15]2=[O:30])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 86590829HCID 86590829, compound

Product 1

HCID 10125766HCID 10125766, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-N-benzyloxy-2-oxo-5-oxazolidinecarboxamide (Step 1, 300 mg, 0.722 mmol) in methanol (28.8 mL) was added 5% palladium-on-carbon (77 mg) under nitrogen. The resulting mixture was degassed and stirred under a hydrogen atmosphere (balloon) for 1 hour. The catalyst was then removed by filtration through Celite, rinsing with methanol (60 mL), and the filtrate was concentrated under reduced pressure. Trituration of this residue with (5% methanol/methylene chloride)/diethyl ether gives the title compound, mp 141-143° C.; MS (ESI+) for C14H16FN3O5 m/z 326 (M+H)+; [α]25D=−70° (c 0.99, DMSO).

Workup

  1. customThe resulting mixture was degassed
  2. customThe catalyst was then removed by filtration through Celite
  3. washrinsing with methanol (60 mL)
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c7a252c569e4cbda41c2be4b1e114a2
Source dataset
uspto-grants-2006_05
Patent number
US07049443B2

Reaction notes

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