Ethanol → HCID 131731186, compound

HRID 239710Notes

Reaction equation

HRID 239710 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]([CH2:16][S:17]([OH:20])(=[O:19])=[O:18])[CH2:14][NH2:15].[CH2:21]([OH:23])C>O1CCOCC1.[OH-].[Na+].O>[NH2:15][C@H:14]([C:21]([NH: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)=[O:23])[CH2:13][C:16]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:10]=1.[CH2:13]([CH2:16][S:17]([OH:20])(=[O:19])=[O:18])[CH2:14][NH2:15]

Participants

6

Reactant 2

HCID 702Ethanol2×HCID 131731187HCID 131731187, compound

Product 1

HCID 131731186HCID 131731186, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N—BOC-L-phenylalanine-N-hydroxusuccinimide ester (400 mg, 1.1 mmol) in a mixture of ethanol (6 mL) and 1,4-dioxane (4 mL) was added to a solution of L-Phe-Homotaurine (273 mg, 1.0 mmol) in 1N NaOH (1.05 mL), water (3 mL) and ethanol (4 mL). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the solid (601.9 mg) was suspended in a mixture of acetone (8 mL) and isopropanol (0.2 mL) and stirred overnight at room temperature. The mixture was heated under refluxed for 30 minutes and then was cooled to room temperature. The white solid was collected by filtration, washed with ether, then dried in the vacuum oven for 45 minutes. The resulting solid (423.1 mg) was dissolved in a mixture of water/tert-butanol (7:3, 5 mL) and treated with Amberlite IR-120 plus (washed, 15 g dry weight) for 2 minutes at room temperature. The resin was removed by filtration and washed 3 times with the mixed solvents of water and tert-butanol (10 mL). Concentrated HCl (4 mL) was added. The solvents were removed under reduced pressure, and the resulting solid was dried in vacuum. The compound was purified by recrystallization from a mixed solvent of THF and MeOH. The resulting solid was heated under reflux in methanol (about 3 mL) to remove the yellowish color. The solid was dried in vacuo. Compound X was obtained as white solid (84.4 mg, 20%). The 1H and 13C NMR were consistent with the structure.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe solid (601.9 mg) was suspended in a mixture of acetone (8 mL) and isopropanol (0.2 mL)
  3. stirringstirred overnight at room temperature
  4. temperatureThe mixture was heated
  5. temperatureunder refluxed for 30 minutes
  6. temperaturewas cooled to room temperature
  7. filtrationThe white solid was collected by filtration
  8. washwashed with ether
  9. customdried in the vacuum oven for 45 minutes
  10. dissolutionThe resulting solid (423.1 mg) was dissolved in a mixture of water/tert-butanol (7:3, 5 mL)
  11. additiontreated with Amberlite IR-120 plus (washed, 15 g dry weight) for 2 minutes at room temperature
  12. customThe resin was removed by filtration
  13. washwashed 3 times with the mixed solvents of water and tert-butanol (10 mL)
  14. additionConcentrated HCl (4 mL) was added
  15. customThe solvents were removed under reduced pressure
  16. customthe resulting solid was dried in vacuum
  17. customThe compound was purified by recrystallization from a mixed solvent of THF and MeOH
  18. temperatureThe resulting solid was heated
  19. temperatureunder reflux in methanol (about 3 mL)
  20. customto remove the yellowish color
  21. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-fbe07f9ca57c4498b2f3756b79aa9e9a
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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