L-Phenylalanine → Phenylalanine ethyl ester

HRID 1976979Notes

Reaction equation

HRID 1976979 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-].[Na+].I[CH2:19][CH3:20]>CN(C=O)C>[CH2:19]([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])[CH3:20]

Participants

5

Reactant 3

HCID 6140L-PhenylalanineHCID 6340IodoethaneHCID 516892Sodium Bicarbonate

Product 1

HCID 76506Phenylalanine ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of N-(2-chloro-6-methylbenzoyl)-4-[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine (7.0 g, 13.84 mmol) and powdered sodium bicarbonate (5.88 g, 70 mmol) in DMF (100 mL) was added excess of iodoethane (10.91 g, 70 mmol) at room temperature. The resulting suspension was stirred for 20 h at which time TLC analysis of the mixture indicated the absence of staring material and the excess iodoethane and some DMF was removed on a rotary evaporator under vacuum. The remaining residue was diluted with 150 mL of ethyl acetate and washed successively with water (2×100 mL), brine solution (100 mL) and dried over MgSO4. Filtration of the drying agent and removal of the solvent afforded a white solid which was crystallized from acetonitrile. The resulting crystalline solid was collected by filtration and dried under high vacuum to afford 5.58 g (77%) of N-(2-chloro-6-methylbenzoyl)-4-[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine ethyl ester as a white solid. mp 230-235° C.

Workup

  1. customthe excess iodoethane and some DMF was removed on a rotary evaporator under vacuum
  2. additionThe remaining residue was diluted with 150 mL of ethyl acetate
  3. washwashed successively with water (2×100 mL), brine solution (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationFiltration of the drying agent and removal of the solvent
  6. customafforded a white solid which
  7. customwas crystallized from acetonitrile
  8. filtrationThe resulting crystalline solid was collected by filtration
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-9227efd64f4942cb8bee71d3bfae3619
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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