1-Octanol → HCID 57235104, compound

HRID 1991436Notes

Reaction equation

HRID 1991436 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:13]([OH:21])[CH2:14]CCCCCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:13]([O:11][C:10](=[O:12])[C@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:1])(=[O:21])[CH3:14]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 6140L-PhenylalanineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 57235104HCID 57235104, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

L-Phenylalanine (5.0 g, 0.03 mol), 1-octanol (3.9 g, 0.03 mol) and p-toluenesulfonic acid monohydrate (6.3 g, 0.038 mol) were suspended in toluene (200 ml) in a flask equipped with a Dean-Stark trap and refluxed for 20 h., resulting in a clear solution. Subsequently, the solvent was removed in vacuo and the remaining white solid was dissolved in CHCl3 (150 ml). This solution was extracted with 10% sodium carbonate, water and brine and dried over MgSO4. Evaporation of the solvent in vacuo yielded a colourless oil (7.7 g, 0.028 mol, 92%). 1H NMR (CDCl3): δ=7.19 (m, 5H), 4.04 (t, 2H, 3J=6.59 Hz), 3.67 (dd, 1H, 3JAB=5.5 Hz, 3JAB=7.7 Hz), 3.03 (dd, 1H, 2JAB=13.6 Hz, 3JAB=5.5 Hz), 2.81 (dd, 1H, 2JAB=13.6 Hz, 3JAB=7.7 Hz), 1.54 (m, 2H), 1.47 (s, 2H), 1.22 (a, 10H), 0.83 (t, 3H, 3J=6.8 Hz); 13C NMR (CDCl3): δ=175.1, 137.15, 129.15, 128.40, 126.65, 65.02, 55.75, 41.06, 31.65, 29.06, 28.41, 25.74, 22.51, 13.97.

Workup

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

Sources & evidence

ORD record
ord-91c2069fce4042938120b50540fe0250
Source dataset
uspto-grants-2010_01
Patent number
US07645805B2

Reaction notes

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