(S)-3-(5-Methyl-2-nitro-phenylamino)-5-phenyl-pentanoic acid ethyl ester → (S)-3-(2-Amino-5-methyl-phenylamino)-5-phenyl-pentanoic acid ethyl ester

HRID 1747293Notes

Reaction equation

HRID 1747293 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([NH:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[N+:23]([O-])=O)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([NH:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[NH2:23])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2]

Participants

4

Reactant 1

HCID 59497545(S)-3-(5-Methyl-2-nitro-phenylamino)-5-phenyl-pentanoic acid ethyl ester

Product 1

HCID 59497376(S)-3-(2-Amino-5-methyl-phenylamino)-5-phenyl-pentanoic acid ethyl esterYield 102.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of (S)-3-(5-Methyl-2-nitro-phenylamino)-5-phenyl-pentanoic acid ethyl ester (0.9 g, 2.5 mmol) in MeOH (20 mL) was added slurry of Pd/C (0.2 g) in MeOH. The reaction mixture was de-gassed using house vacuum. The reaction mixture was stirred under H2 balloon for 3 h. When the reaction color changed from orange to colorless, the reaction mixture was filtered through a pad of celite. The filtrate was concentrated to afford 0.84 g the desired product. This product was used for the next reaction without further purification.

Workup

  1. customThe reaction mixture was de-gassed
  2. filtrationwas filtered through a pad of celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2f05c65065a94dd8ba7850900d2c9530
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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