tert-Butyl [3-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)phenyl]carbamate → Carbamic acid,n-[3-[2-[5-amino-2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]ethyl]phenyl]-,1,1-dimethylethyl ester

HRID 541897Notes

Reaction equation

HRID 541897 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:6]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=2)[CH:7]=1>[Pd].CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:6]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 57962363tert-Butyl [3-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)phenyl]carbamate

Product 1

HCID 57962696Carbamic acid,n-[3-[2-[5-amino-2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]ethyl]phenyl]-,1,1-dimethylethyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into the reaction flask was added tert-butyl [3-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)phenyl]carbamate (1.0 g, 2.4 mmol), 50 mL of methanol, and 10% palladium on carbon (0.10 g, 0.097 mmol). The reaction mixture was hydrogenated at 25 psi for 3 h. The mixture was filtered and concentrated to give the desired product (0.9 g, 89%). LCMS for C24H33NaN3O4 (M+Na)+: m/z=450.2

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-38d80630256c4ca4a2b758e5764ab96d
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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