Triethylamine → 5-((1,1'-Biphenyl)-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid, (2S,4R)-

HRID 1844801Notes

Reaction equation

HRID 1844801 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])/[CH:9]=[C:10](\[CH3:14])/[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.C(N(CC)CC)C.[H][H]>C(OC(C)C)(=O)C.[Pd]>[C:1]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:9][C@H:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86637608HCID 86637608, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 688200625-((1,1'-Biphenyl)-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid, (2S,4R)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7915Isopropyl AcetateSolvent

Procedure

To a suspension of (E)-(S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid 3(ii-b) (10 g, 26.2 mmol) and triethylamine (3.6 ml, 26.2 mmol) in isopropyl acetate is added palladium on carbon (1 g, 10% loading). Hydrogen atmosphere is then applied for 5 h. Upon filtering off the catalyst, the solvent is removed in vacuo to give the title compound {3(i-d): 3(i-c) 80:20 ratio; 3(i-d): 3(i-c) 99.9:0.1 ratio upon recrystallization; as determined by HPLC analysis}.

Workup

  1. filtrationUpon filtering off the catalyst
  2. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-be87393a93de4e7eb6e7263ea4a6f310
Source dataset
uspto-grants-2015_02
Patent number
US08946481B2

Reaction notes

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