Cyclohexylamine → HCID 10760075, compound

HRID 1647133Notes

Reaction equation

HRID 1647133 reaction equation
Cl[C:2]([O:4][C@@H:5]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])=[O:3].[CH:20]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>O1CCCC1>[CH:20]1([NH:26][C:2]([O:4][C@@H:5]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[O:3])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 57259964HCID 57259964, compound

Product 1

HCID 10760075HCID 10760075, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (2S)-2-chlorocarbonyloxy-4-methylvalerate (0.56 g) in tetrahydrofuran (11 ml) was added cyclohexylamine (0.40 g) at room temperature. After being stirred for 10 minutes, the solvent was removed by evaporation under reduced pressure, and the residue was dissolved in ethyl acetate (30 ml). The solution was washed with 1N HCl, water and brine successively. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residual solid was triturated with hexane to give benzyl (2S)-2-cyclohexylcarbamoyloxy-4-methylvalerate (0.45 g).

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  3. washThe solution was washed with 1N HCl, water and brine successively
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residual solid was triturated with hexane

Sources & evidence

ORD record
ord-78a357f5159545818bf6944e4d08a7af
Source dataset
uspto-grants-1995_07
Patent number
US05430022

Reaction notes

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