HCID 86661406, compound → (R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid

HRID 1908962Notes

Reaction equation

HRID 1908962 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=1[F:30])[CH2:10][C:11]([O:13]CC1C=CC=CC=1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=1[F:30])[CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86661406HCID 86661406, compound

Product 1

HCID 7146288(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acidYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

58 mg of (R)-benzyl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate, 3 mL of methanol, and 20 mg of 10 wt % palladium/carbon were added to 25 mL flask and the resulting reaction solution was stirred. A hydrogen gas was bubbled for 2 hours at room temperature; the reaction solution was filtered by passing through celite, washed with 15 mL of ethyl acetate, and the filtrate was concentrated under reduced pressure to obtain 44 mg of a title compound.

Workup

  1. customthe resulting reaction solution
  2. customA hydrogen gas was bubbled for 2 hours at room temperature
  3. filtrationthe reaction solution was filtered
  4. washwashed with 15 mL of ethyl acetate
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-22303821089649ac917dde54761ec548
Source dataset
uspto-grants-2013_12
Patent number
US08598347B2

Reaction notes

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