Acetonitrile → HCID 86710681, compound

HRID 1027267Notes

Reaction equation

HRID 1027267 reaction equation
C(#N)C.[OH:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][C:6]=1[O:21][CH3:22].Br[CH:24]([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O>[CH:24]([O:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[CH:7][C:6]=1[O:21][CH3:22])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 63582-Bromopropane2×HCID 11430Potassium CarbonateHCID 14018350HCID 14018350, compound

Product 1

HCID 86710681HCID 86710681, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a 250 mL round bottom flask containing acetonitrile (18.7 mL) was added tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate (1.0 g, 3.74 mmol), 2-bromopropane (0.51 g, 4.11 mmol), and potassium carbonate (1.5 g, 11.22 mmol). The resulting suspension was stirred at 65° C. for 18 hours. A second addition of 2-bromopropane (0.51 g, 4.11 mmol) was performed and heating was continued for another 18 hours. The reaction mixture was concentrated reaction in vacuo. The resulting oil was dissolved in EtOAc and washed with H2O, aqeuous saturated sodium bicarbonate and brine, then dried with sodium sulfate and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-100% EtOAc in Heptane) to afford tert-butyl 4-isopropoxy-3-methoxyphenethylcarbamate (0.81 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 6.84 (d, J=8.03 Hz, 1H), 6.67-6.75 (m, 2H), 4.37-4.70 (m, 2H), 3.86 (s, 3H), 3.27-3.46 (m, 2H), 2.68-2.81 (m, 2H), 1.45 (s, 9H), 1.37 (d, J=6.02 Hz, 6H).

Workup

  1. temperatureheating
  2. waitwas continued for another 18 hours
  3. concentrationThe reaction mixture was concentrated
  4. customreaction in vacuo
  5. washwashed with H2O, aqeuous saturated sodium bicarbonate and brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography (0-100% EtOAc in Heptane)

Sources & evidence

ORD record
ord-2b080fbda7a64b4aab0f4c7ebf6a00c7
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

Loading…