Tert-butyl 2-({4-[(4-acetamidophenyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate → Tert-butyl 2-({4-[(4-acetamidophenyl)ethyl]phenyl}acetyl)hydrazinecarboxylate

HRID 1465433Notes

Reaction equation

HRID 1465433 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([NH:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>O1CCCC1CO.[C].[Pd]>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([NH:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 67030024Tert-butyl 2-({4-[(4-acetamidophenyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate

Product 1

HCID 67030250Tert-butyl 2-({4-[(4-acetamidophenyl)ethyl]phenyl}acetyl)hydrazinecarboxylateYield 82.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

tert-Butyl 2-({4-[(4-acetamidophenyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate (29 mg, 0.071 mmol) was dissolved in a mixture of tetrahydrofuran-methanol (1:1) and hydrogenated using a continuous hydrogenation reactor (trade name: H-CUBE, manufactured by ThalesNano) equipped with a 10%-palladium carbon cartridge. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3) to give tert-butyl 2-({4-[(4-acetamidophenyl)ethyl]phenyl}acetyl)hydrazinecarboxylate (24 mg, yield 82%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3)

Sources & evidence

ORD record
ord-aeb9ab7dc638411089ad4abea022d514
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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