HCID 86714409, compound → HCID 86714410, compound

HRID 1750197Notes

Reaction equation

HRID 1750197 reaction equation
[C:1]([O:5][C:6](=[O:30])[C@@H:7]([NH:12][C:13](=[O:29])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[C:16]([N+:26]([O-])=O)[CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:30])[C@@H:7]([NH:12][C:13](=[O:29])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[C:16]([NH2:26])[CH:15]=1)[CH2:8][CH:9]([CH3:10])[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86714409HCID 86714409, compound

Product 1

HCID 86714410HCID 86714410, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

11.5 g of (S)-2-[4-(1-ethyl-propylamino)-3-nitro-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester were dissolved in 100 ml ethanol, 1.0 g of palladium on carbon (10%) were added and the mixture was hydrogenated at 5 bar for 4 h. the catalyst was removed by filtration over celite, and the reaction mixture was concentrated and purified by chromatography (silica, heptane/ethyl acetate) to yield 6.5 g (61%) of (S)-2-[3-amino-4-(1-ethyl-propylamino)-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester as a colourless oil.

Workup

  1. customthe catalyst was removed by filtration over celite
  2. concentrationthe reaction mixture was concentrated
  3. custompurified by chromatography (silica, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-ff50fb02ca194f98b7ce43aa406e0194
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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