Methanol → 2-acetamido-N-tert-butyl-2-(2-(pyridin-2-yl)ethyl)hex-5-enamide

HRID 579529

Reaction equation

HRID 579529 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9](=O)[CH2:10][CH2:11][CH:12]=[CH2:13].[C:15]([O-:18])(=O)[CH3:16].[NH4+:19].[C:20]([N+:24]#[C-:25])([CH3:23])([CH3:22])[CH3:21].C[OH:27]>FC(F)(F)CO.ClCCl>[C:15]([NH:19][C:9]([CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([CH2:10][CH2:11][CH:12]=[CH2:13])[C:25]([NH:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:27])(=[O:18])[CH3:16]

Participants

7

Reactant 4

HCID 887MethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 668331331-(Pyridin-2-yl)hept-6-en-3-one

Product 1

HCID 668337082-acetamido-N-tert-butyl-2-(2-(pyridin-2-yl)ethyl)hex-5-enamideYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

A solution of 1-(pyridin-2-yl)hept-6-en-3-one (825 mg, 4.36 mmol) and ammonium acetate (1.01 g, 13.09 mmol) in 2,2,2-trifluoroethanol (3 mL) was treated with tert-butyl isocyanide (730 mg, 0.99 mL, 8.80 mmol). After stirring at room temperature for 6 days, the reaction mixture was purified by flash column chromatography (crude reaction mixture loaded on the top of the column; silica gel, 0-10% methanol in dichloromethane) to give 2-acetamido-N-tert-butyl-2-(2-(pyridin-2-yl)ethyl)hex-5-enamide as white solid (1.37 g, 95%). ESI MS found for C19H29N3O2 m/z [332.2 (M+1)].

Workup

  1. customthe reaction mixture was purified by flash column chromatography (crude
  2. customreaction mixture

Sources & evidence

ORD record
ord-cca06af7926e42fd8381b1e474a7ad20
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Linked notes

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