3-Benzyloxycarbonylamino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester → (3S)-3-Amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic Acid Tert-Butyl Ester
Reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([NH:23]C(OCC1C=CC=CC=1)=O)[CH:9]([OH:22])[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:34])[CH2:7][C@H:8]([NH2:23])[CH:9]([OH:22])[CH2:10][O:11][C:12]1[C:13]([F:21])=[C:14]([F:20])[CH:15]=[C:16]([F:19])[C:17]=1[F:18])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
10% Pd on carbon (2.92 g) was added portionwise to a solution of 3-benzyloxycarbonylamino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester (14.6 g) in anhydrous MeOH (350 mL) which has been degassed under nitrogen (5×). The reaction was further degassed under nitrogen (3×) and hydrogen (5×) and stirred at room temperature for 20 minutes. The palladium residues were removed by filtration and the filtrate concentrated to give the sub-title compound as a white solid (9.5 g, 90%); 1H NMR (400 MHz, CDCl3) δ 1.49 (9H, s), 2.35-2.43 (1H, m), 5.67-5.64 (1H, m), 3.37-3.43 (1H, m), 3.77-3.87 (1H, m), 4.28-4.63 (2H, m), 6.77-6.86 (1H, m); 19F NMR (346 MHz, CDCl3) (proton decoupled) δ −139.95, −139.97, −140.00, −140.03, −140.05, −140.08, −140.11, −140.13, −157.15, −157.18, −157.21, −157.23, −157.27, −157.29.
Workup
- customhas been degassed under nitrogen (5×)
- customThe reaction was further degassed under nitrogen (3×)
- customThe palladium residues were removed by filtration
- concentrationthe filtrate concentrated
Sources & evidence
- ORD record
- ord-bf42ff23b52842e798cd5dcc5e2268b0
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071618B2
Reaction notes
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