HCID 57805725, compound → HCID 57805710, compound

HRID 2104206Notes

Reaction equation

HRID 2104206 reaction equation
[F:1][CH2:2][C@@H:3]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])[CH2:4][C:5]([O:7]CC1C=CC=CC=1)=[O:6]>C(O)C.[Pd]>[F:1][CH2:2][C@@H:3]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])[CH2:4][C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 57805725HCID 57805725, compound

Product 1

HCID 57805710HCID 57805710, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

(S)-4-fluoro-3-(1,3-dioxoisoindolin-2-yl)butanoic acid 19-4 (0.20 mmol) was dissolved in ethanol (5 ml). This solution was purged with nitrogen for 10 minutes, then 10% palladium on carbon was added (0.02 mmol of palladium) under an atmosphere of nitrogen. Hydrogen was then bubbled rapidly through the solution, while stirring, for approximately 1 h. The reaction progress was followed with LCMS. The reaction mixture was filtered through celite to remove the palladium. The celite was rinsed twice with methylene chloride. The filtrate was then concentrated to give the crude product. The crude product 19-6 was used for the next reaction step.

Workup

  1. customThis solution was purged with nitrogen for 10 minutes
  2. customHydrogen was then bubbled rapidly through the solution
  3. filtrationThe reaction mixture was filtered through celite
  4. customto remove the palladium
  5. washThe celite was rinsed twice with methylene chloride
  6. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-16427b634c8d4842b28e2ea7edaff0ec
Source dataset
uspto-grants-2009_08
Patent number
US07576221B2

Reaction notes

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