HCID 90372319, compound → HCID 90372405, compound

HRID 1467361Notes

Reaction equation

HRID 1467361 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]([CH3:23])([CH3:22])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[C:12]=1[C:20]#[N:21])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]([CH3:23])([CH3:22])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[C:12]=1[C:20]#[N:21])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 90372319HCID 90372319, compound

Product 1

HCID 90372405HCID 90372405, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl(1-(2-cyano-3-nitrophenoxy)-2-methylpropan-2-yl)carbamate (45 g, 134 mmol) in ethyl acetate (200 mL) and ethanol (100 mL) was added 10% palladium on carbon (4.5 g). The reaction was stirred under H2 at 40 psi, and upon completion, the mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo to provide tert-butyl(1-(3-amino-2-cyanophenoxy)-2-methylpropan-2-yl)carbamate as a white solid (41 g, 100%). 1H NMR (DMSO-d6), 400 MHz: δ 1.26 (s, 6H), 1.34 (s, 9H), 4.00 (s, 2H), 5.96 (br s, 2H), 6.15 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.0 Hz, 1H), 6.63 (br s, 1H), 7.14 (t, J=8.0 Hz, 1H). MS 206 (MH+).

Workup

  1. filtrationupon completion, the mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8a036e2a63614f16b3629ee1cdf37d11
Source dataset
uspto-grants-2015_04
Patent number
US09000151B2

Reaction notes

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