(2S)-N-((1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide → HCID 58466401, compound

HRID 1874628Notes

Reaction equation

HRID 1874628 reaction equation
[N:1]([CH2:4][C@H:5]([NH:19][C:20](=[O:29])[C@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([CH3:18])[CH2:15][CH2:16][CH3:17])=[CH:8][CH:7]=1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH2:4][C@H:5]([NH:19][C:20](=[O:29])[C@H:21]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:22])[C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH:14]([CH3:18])[CH2:15][CH2:16][CH3:17])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 86658399(2S)-N-((1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide

Product 1

HCID 58466401HCID 58466401, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2S)-N-((1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide (12.0 g, 30.4 mmol) in ethanol (40 mL) in a Parr shaker bottle was added 10% Pd/C (3.0 g, 2.82 mmol, Degussa type). The reaction mixture was placed under an H2 atmosphere at 40 psi for 1 h. The mixture was then filtered through a pad of diatomaceouse earth (Celite®) and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (10% methanol in dichloromethane) to afford (2S)-N-((1R)-2-amino-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide (7.0 g, 63% yield) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.22 (d, J=8.1 Hz, 1H), 7.22-7.31 (m, 4H), 7.13-7.22 (m, 1H), 6.99 (d, 2H), 6.74 (d, 2H), 4.56-4.70 (m, 1H), 3.69-3.79 (m, 2H), 3.65 (dd, J=9.3, 6.5 Hz, 1H), 3.34 (br. s., 2H), 2.61-2.75 (m, 2H), 1.83 (dddd, J=12.5, 6.5, 6.4, 6.3 Hz, 1H), 1.33-1.36 (m, 3H), 1.24-1.48 (m, 3H), 1.10-1.20 (m, 1H), 0.93 (d, J=6.8 Hz, 3H), 0.87 (t, J=7.1 Hz, 3H); LRMS (ESI) m/e 369.2 [(M+H)+, calcd for C23H33N2O2 369.3].

Workup

  1. filtrationThe mixture was then filtered through a pad of diatomaceouse earth (Celite®)
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-20bc6cb2a3bc40769bd6f3e0e9dccfda
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

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