Methanol → HCID 14037835, compound

HRID 375097Notes

Reaction equation

HRID 375097 reaction equation
[NH2:1][C:2]([CH2:14][CH3:15])([C:10]([O:12]C)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].O.CO>O1CCCC1>[NH2:1][C:2]([CH2:14][CH3:15])([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 12182755HCID 12182755, compound

Product 1

HCID 14037835HCID 14037835, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of D,L-Phe(αEt)-OMe (24 g, 116 mmol) in tetrahydrofuran (200 mL) was added 5N NaOH (24 mL, 120 mmol), followed by water (50 mL) and methanol (50 mL) and the solution was heated to reflux. After 16 h, the solution was cooled to room temperature and the solvents were removed in vacuo. The residue was dissolved in water and washed three times with diethyl ether. The pH was adjusted to 6 with 5N HCl and the solution was concentrated to a volume of about 50 mL in vacuo. The precipitate was filtered, washed with water and dried to give 17.5 g (78% yield) of white solid.

Workup

  1. temperaturethe solution was heated to reflux
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. washwashed three times with diethyl ether
  5. concentrationthe solution was concentrated to a volume of about 50 mL in vacuo
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-7bc58628663f44f188ac6f9e14a43cf6
Source dataset
uspto-grants-1996_01
Patent number
US05484772

Reaction notes

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