3-[Benzyl-(1(R)-phenylethyl)-amino]-3-(2-fluoro-biphenyl-4-yl)-propionic acid ethyl ester → 3-Amino-3-(2-fluoro-biphenyl-4-yl)-propionic acid ethyl ester

HRID 1387459Notes

Reaction equation

HRID 1387459 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][CH:6]([N:20](CC1C=CC=CC=1)[C@@H](C1C=CC=CC=1)C)[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9]([F:19])[CH:8]=1)[CH3:2]>CCO.CC(O)=O.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4](=[O:36])[CH2:5][CH:6]([NH2:20])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9]([F:19])[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 697797503-[Benzyl-(1(R)-phenylethyl)-amino]-3-(2-fluoro-biphenyl-4-yl)-propionic acid ethyl ester

Product 1

HCID 544941723-Amino-3-(2-fluoro-biphenyl-4-yl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 18476134Acetic acid ethanolSolvent

Procedure

A solution of the dibenzylamine 13-3 (5.65 gm, 11.75 mmol) in EtOH/HOAc (90/10 mL) was purged with argon and treated with Pd(OH)2 (3 g) and placed under 1 atm of H2 gas for 12 h. Additional portions (2.5 g) or Pd(OH)2 were added after 24 h, 48 h and 144 h. The reaction mixture was purged with argon, filtered through Celite, and the filtrate dissolved in aq HCl (pH=1) The aqueous solution was washed with EtOAc, neutralized with satd aq NaHCO3, and extracted with EtOAc (3×30 mL). The combined organic solutions were washed with brine, dried over MgSO4, filtered and concentrated to give the desired product 13-4.

Workup

  1. customThe reaction mixture was purged with argon
  2. filtrationfiltered through Celite
  3. dissolutionthe filtrate dissolved in aq HCl (pH=1) The aqueous solution
  4. washwas washed with EtOAc
  5. extractionextracted with EtOAc (3×30 mL)
  6. washThe combined organic solutions were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-53258c927978405a9ca1f5a6df2e70ad
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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