Potassium Carbonate → HCID 67704053, compound

HRID 1941355Notes

Reaction equation

HRID 1941355 reaction equation
[NH2:1][CH:2]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:3]([OH:16])[CH2:4][CH:5]([CH:13]([CH3:15])[CH3:14])[C:6]([NH:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7].Br[CH2:25][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[NH4+:1].[OH-:7].[OH:16][CH:3]([CH:2]([NH:1][CH2:25][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])[CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH2:4][CH:5]([CH:13]([CH3:14])[CH3:15])[C:6]([NH:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1375215-Bromo-2-methyl-2-penteneHCID 67703993HCID 67703993, compound

Product 2

HCID 14923Ammonium HydroxideHCID 67704053HCID 67704053, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[αR(αR*,γR*,δS*)]-δ-Amino-γ-hydroxy-α-(1-methylethyl)-N-(2-methylpropyl)cyclohexanehexanamide (80 mg, 0.245 mmol), 5-bromo-2-methyl-2-pentene (44 mg, 0.27 mmol), and K2CO3 (250 mg) were dissolved in acetonitrile (10 mL) and stirred at RT for 24 h followed by heating at reflux under N2 for 8 h. The solvents were removed in vacuo. The residue was dissolved with CH2Cl2 and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography (1:0:0 to 95:5:05 CH2Cl2 :MeOH:NH4OH gradient) of the concentrate afforded the title compound (42 mg, 42%) as a wax.

Workup

  1. temperatureby heating
  2. temperatureat reflux under N2 for 8 h
  3. customThe solvents were removed in vacuo
  4. dissolutionThe residue was dissolved with CH2Cl2
  5. washwashed with water
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b7cc46faf4c49b98199ecbec1e07025
Source dataset
uspto-grants-1997_12
Patent number
US05703129

Reaction notes

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