Methyl L-phenylalaninate hydrochloride → L-Phenylalanine

HRID 2388620Notes

Reaction equation

HRID 2388620 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 uL, 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-1891ea602c524e908eabbc01291f6493
Source dataset
uspto-grants-2012_09
Patent number
US08269039B2

Reaction notes

Loading…