Ammonium Hydroxide → HCID 67608904, compound

HRID 1965199Notes

Reaction equation

HRID 1965199 reaction equation
[CH2:1]([O:8][C:9](=[O:39])[N:10]([CH:12]([C:14](=[O:38])[NH:15][CH:16]([C:21]([N:23]1[CH2:27][CH2:26][CH:25]2[N:28]([C:32](=[O:37])[NH:33][CH:34]([CH3:36])[CH3:35])[CH2:29][CH:30]([OH:31])[CH:24]12)=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:40]([N:47]=[C:48]=[O:49])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[NH4+].[OH-]>C(#N)C.CO>[CH2:1]([O:8][C:9](=[O:39])[N:10]([CH:12]([C:14](=[O:38])[NH:15][CH:16]([C:21]([N:23]1[CH2:27][CH2:26][CH:25]2[N:28]([C:32](=[O:37])[NH:33][CH:34]([CH3:35])[CH3:36])[CH2:29][CH:30]([O:31][C:48](=[O:49])[NH:47][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:24]12)=[O:22])[C:17]([CH3:18])([CH3:19])[CH3:20])[CH3:13])[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 76639Benzyl isocyanateHCID 67514413HCID 67514413, compound

Product 1

HCID 67608904HCID 67608904, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution containing 57 (280 mg, 0.51 mmol) and benzyl isocyanate (350 μL, 2.83 mmol) in acetonitrile (500 μL) was warmed to reflux. After 12 h, the reaction mixture was cooled to ambient temperature, diluted with MeOH, and treated with aqueous NH4OH (30%, 5 mL). The solution was concentrated in vacuo and the residue was dissolved in EtOAc, washed successively with 1N HCl, water, aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by reverse-phase HPLC (2″ Dynamax® C18, 50-100% MeOH/water containing 0.1% HOAc over 20 min; Flow: 40 mL/min). The pure fractions were combined and concentrated to afford 58 as a white solid (250 mg, 72%). Mass spectrum, m/z [679.3] (M+H)+.

Workup

  1. temperaturewas warmed to reflux
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed successively with 1N HCl, water, aqueous NaHCO3, and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by reverse-phase HPLC (2″ Dynamax® C18, 50-100% MeOH/water containing 0.1% HOAc over 20 min
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f27760bf8c2f4852be51701f07b89beb
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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