HCID 86714407, compound → HCID 86714378, compound

HRID 1750193Notes

Reaction equation

HRID 1750193 reaction equation
[C:1]([O:5][C:6](=[O:32])[C@@H:7]([NH:12][C:13](=[O:31])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[C:16]([N+:28]([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:32])[C@@H:7]([NH:12][C:13](=[O:31])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH:21]([CH:22]([CH3:24])[CH3:23])[CH:25]([CH3:26])[CH3:27])=[C:16]([NH2:28])[CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86714407HCID 86714407, compound

Product 1

HCID 86714378HCID 86714378, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.35 g of (S)-2-[4-(1-Isopropyl-2-methyl-propylamino)-3-nitro-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester were dissolved in 14 ml ethanol, 0.30 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 to yield 1.00 g (79%) of (S)-2-[3-Amino-4-(1-isopropyl-2-methyl-propylamino)-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester as a viscous oil, which was used without further purification.

Workup

  1. customThe catalyst was removed by filtration over celite
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-e5b1351929294e4a8407abac1875c430
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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