1-Octanol → HCID 53935876, compound

HRID 1991437Notes

Reaction equation

HRID 1991437 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:10]([O:8][C:7](=[O:9])[C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[NH2:1])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 6106L-LeucineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 53935876HCID 53935876, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

L-Leucine (5.0 g, 0.038 mol), 1-octanol (5.0 g, 0.038 mol) and p-toluenesulfonic acid monohydrate (8.0 g, 0.042 mol) were suspended in toluene (200 ml) in a flask equipped with a Dean-Stark trap and refluxed for 20 h. Subsequently, the solvent was removed in vacuo and the remaining white solid was dissolved in CHCl3 (150 ml). This solution was extracted with 10%1/sodium carbonate, water and brine and dried Over MgSO4, Evaporation of the solvent in vacuo yielded a colourless oil (9.0 g, 0.037 mol, 97%). 1H NMR (CDCl3): δ=4.18 (t, 2H, 3J=7.0 Hz), 3.63 (dd, 1H, 3JAB=8.4 Hz, 3JAB=5.9 Hz), 1.85 (m, 1H), 1.74-3.18 (m, 6H), 1.37 (s, 10H, 0.99 (t's, 9H); 13C NMR (CDCl3): δ=176.98, 64.82, 52.79, 44.06, 31.64, 29.04, 28.47, 25.76, 24.66, 22.81, 22.51, 21.77, 13.96

Workup

  1. customequipped with a Dean-Stark trap
  2. temperaturerefluxed for 20 h
  3. customSubsequently, the solvent was removed in vacuo
  4. dissolutionthe remaining white solid was dissolved in CHCl3 (150 ml)
  5. extractionThis solution was extracted with 10%1/sodium carbonate, water and brine
  6. dry with materialdried Over MgSO4, Evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-122c091b40364004b6fabd72f2b161a5
Source dataset
uspto-grants-2010_01
Patent number
US07645805B2

Reaction notes

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