HCID 86590829, compound → HCID 10125766, compound

HRID 723824Notes

Reaction equation

HRID 723824 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) is added 5% palladium-on-carbon (77 mg) under nitrogen. The resulting mixture is degassed and stirred under a hydrogen atmosphere (balloon) for 1 h. The catalyst is then removed by filtration through Celite, rinsing with methanol (60 mL), and the filtrate is 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 is degassed
  2. customThe catalyst is then removed by filtration through Celite
  3. washrinsing with methanol (60 mL)
  4. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-571e3c39a5524568ae45bf2498294281
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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