Methyl 3-({3-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)-5-nitrobenzoate → Methyl 3-amino-5-(2-{3-[(tert-butoxycarbonyl)amino]phenyl}ethyl)benzoate

HRID 541740Notes

Reaction equation

HRID 541740 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]#[C:16][C:17]2[CH:18]=[C:19]([CH:24]=[C:25]([N+:27]([O-])=O)[CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:27][C:25]1[CH:24]=[C:19]([CH:18]=[C:17]([CH2:16][CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:10]=2)[CH:26]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

4

Reactant 1

HCID 57962421Methyl 3-({3-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)-5-nitrobenzoate

Product 1

HCID 57961977Methyl 3-amino-5-(2-{3-[(tert-butoxycarbonyl)amino]phenyl}ethyl)benzoateYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 3-({3-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)-5-nitrobenzoate (1.85 g, 4.67 mmol) in methanol (50 mL) was added 10% palladium on carbon (1.85 g, 1.58 mmol), and the mixture was hydrogenated under 55 psi of H2 for 72 hours with shaking. The solution was filtered through a pad of celite, and filtrate was concentrated. The residue was purified by flash column chromatography to give the desired product as a yellow oil (1.70 g, 98%). LCMS for C21H27N2O4 (M+H)+: m/z=371.1.

Workup

  1. filtrationThe solution was filtered through a pad of celite, and filtrate
  2. concentrationwas concentrated
  3. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-9443e9a2f0754b46ac4cad3189c016d6
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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