Imidazole → Tert-butyl 2-(2-(tert-butyldimethylsilyloxy)-1-(4-cyanophenyl)ethylamino)acetate

HRID 572577Notes

Reaction equation

HRID 572577 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([NH:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][OH:24])=[CH:18][CH:17]=1)#[N:15]>CN(C=O)C.CCOC(C)=O>[Si:5]([O:24][CH2:23][CH:22]([NH:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:19]1[CH:18]=[CH:17][C:16]([C:14]#[N:15])=[CH:21][CH:20]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 66652797Tert-butyl 2-(1-(4-cyanophenyl)-2-hydroxyethylamino)acetate

Product 1

HCID 66652772Tert-butyl 2-(2-(tert-butyldimethylsilyloxy)-1-(4-cyanophenyl)ethylamino)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

t-Butyldimethyl silyl chloride (0.579 g; 3.84 mmol) and imidazole (0.261 g; 3.83 mmol) were added to a solution of tert-butyl 2-(1-(4-cyanophenyl)-2-hydroxyethylamino)acetate (0.709 g; 2.56 mmol) in DMF (10 mL). The reaction mixture was stirred at ambient temperature for 18 hours. The mixture was diluted with EtOAc and washed sequentially with water and brine. The organic phase was poured through a hydrophobic frit and the solvent evaporated in vacuo. The residue was purified by flash chromatography eluting with iso-hexane/EtOAc (10:1) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.63-7.61 (m, 2H), 7.48 (d, J=8.4 Hz, 2H), 3.86-3.83 (m, 1H), 3.66-3.55 (m, 2H), 3.23 (d, J=16.8 Hz, 1H), 3.06 (d, J=16.8 Hz, 1H), 2.53 (br s, 1H), 1.47 (s, 9H), 0.90 (s, 9H), 0.10 (s, 3H), 0.09 (s, 3H).

Workup

  1. washwashed sequentially with water and brine
  2. additionThe organic phase was poured through a hydrophobic frit
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by flash chromatography
  5. washeluting with iso-hexane/EtOAc (10:1)

Sources & evidence

ORD record
ord-623ed33d8f1142a3bc03eb8cf500059c
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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