3,5-Difluoro-L-phenylalanine, N-BOC protected → (S)-2-Boc-amino-3-(3,5-difluorophenyl)propan-1-OL

HRID 339970Notes

Reaction equation

HRID 339970 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=1)[CH2:10][OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 27790093,5-Difluoro-L-phenylalanine, N-BOC protected

Product 1

HCID 57881012(S)-2-Boc-amino-3-(3,5-difluorophenyl)propan-1-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid [Aldrich] (3.00 g, 9.96 mmol) in tetrahydrofuran (30 mL) at 0° C. was added 1.0 M borane-THF complex in tetrahydrofuran (32 mL, 32 mmol). The reaction mixture was stirred at room temperature for 3 hrs, and then cooled with an ice bath, quenched with AcOH:MeOH (1:5, 10 mL), and partitioned between saturated aqueous NaHCO3 solution and dichloromethane (DCM). The aqueous phase was then extracted several times with DCM. The combined organic fractions were dried over Na2SO4 and concentrated under reduced pressure. The residue was used directly for the next reaction. LCMS (ES) m/e 288.1 (M+H)+.

Workup

  1. temperaturecooled with an ice bath
  2. customquenched with AcOH:MeOH (1:5, 10 mL)
  3. custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane (DCM)
  4. extractionThe aqueous phase was then extracted several times with DCM
  5. dry with materialThe combined organic fractions were dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was used directly for the next reaction

Sources & evidence

ORD record
ord-c67784604bb549be9171201caccfbad0
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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