Water → Benzyl N,N-dibenzyl-L-phenylalaninate

HRID 428470Notes

Reaction equation

HRID 428470 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.C(=O)([O-])[O-].[K+].[K+].O.[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[CH2:20]([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)[N:1]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6140L-PhenylalanineHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 10928230Benzyl N,N-dibenzyl-L-phenylalaninate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution containing L-phenylalanine (161 kg, 975 moles), potassium carbonate (445 kg, 3220 moles), water (675 L), ethanol (340 L), and benzyl chloride (415 kg, 3275 moles) was heated to 90±15° C. for 10-24 hours. The reaction mixture was cooled to 60° C. and the lower aqueous layer was removed. Heptane (850 L) and water (385 L) were added to the organics, stirred, and the layers separated. The organics were then washed once with a water/methanol mixture (150 L/150 L). The organics were then stripped to give the desired product as an oil, which was carried on in the next step without purification.

Workup

  1. temperatureThe reaction mixture was cooled to 60° C.
  2. customthe lower aqueous layer was removed
  3. additionHeptane (850 L) and water (385 L) were added to the organics,
  4. customthe layers separated
  5. washThe organics were then washed once with a water/methanol mixture (150 L/150 L)

Sources & evidence

ORD record
ord-6f5c2bd401c7488ba7729bc450117234
Source dataset
uspto-grants-2001_11
Patent number
US06313296B1

Reaction notes

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