Methyl L-phenylalaninate hydrochloride → L-Phenylalanine

HRID 476306Notes

Reaction equation

HRID 476306 reaction equation
[N+](CCC(CC)C(O)=O)([O-])=O.[NH2:12][C@H:13]([C:21]([O:23]C)=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.OS([O-])(=O)=O.[Na+]>ClCCl.CN(C1C=CN=CC=1)C>[NH2:12][C@H:13]([C:21]([OH:23])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 81531DiisopropylethylamineHCID 516919Sodium BisulfateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 46223056HCID 46223056, compound

Product 1

HCID 6140L-Phenylalanine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

γ-Nitro-α-ethylbutyric acid 3 (97 mg, 0.6 mmol) was dissolved in dry dichloromethane (20 ml). Then L-Phe-OMe.HCl (142 mg, 0.66 mmol), EDCI.HCl (138 mg, 0.72 mmol), DIEA (128 μL, 0.72 mmol) and catalytic amount of DMAP were successively added. The mixture was stirred 24 h at room temperature, then was acidified with aqueous NaHSO4, extracted with EtOAc (3×). The organic layers were washed with saturated NaHCO3 and brine. The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified via column chromatography eluted with EtOAc/hexane to give L-phenylalanine derivative 7 as a while solid.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe organic layers were washed with saturated NaHCO3 and brine
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via column chromatography
  7. washeluted with EtOAc/hexane

Sources & evidence

ORD record
ord-5c0e657b856f4bc99fc38ff969a4deab
Source dataset
uspto-grants-2014_01
Patent number
US08637696B2

Reaction notes

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