Ethanol → 5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid methyl ester

HRID 2174882Notes

Reaction equation

HRID 2174882 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4](=[CH2:28])[CH2:5][C@H:6]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.C(O)C.[H][H]>[Pd].C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:29])[CH:4]([CH3:28])[CH2:5][CH:6]([NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 66958027(R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid methyl ester2×HCID 178418361HCID 178418361, compound

Product 1

HCID 581603965-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

500 mg (R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid methyl ester (2-a, R1=Boc, R2=H, R3=CO2Me) is added to ethanol (5 ml) at ambient temperature. Triethylamine (176 μl) is then added to the mixture. 50 mg Palladium on carbon (10%, 50% water-wet, Degussa E101 NE/W) is then added. Hydrogen gas at ambient pressure is applied to the mixture. The mixture is then stirred overnight at ambient temperature and pressure. The mixture is then filtered and concentrated under reduced pressure to afford 2R,4S)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid methyl ester (1-a, R1=Boc, R2=H, R3=CO2Me) and (2S,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid methyl ester (1-b, R1=Boc, R2=H, R3=CO2Me). Spectroscopic data as in Example 60. Ratio of diastereomers 66:34 (1-a, R1=Boc, R2=H, R3=CO2Me:1-b, R1=Boc, R2=H, R3=CO2Me) by integration of signals at 1.76-1.85 (1-b, R1=Boc, R2=H, R3=CO2Me) and 1.92-1.99 (1-a, R1=Boc, R2=H, R3=CO2Me).

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-193ac5a152e447a3be6b39abd5fa8751
Source dataset
uspto-grants-2015_06
Patent number
US09061973B2

Reaction notes

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