N-tert-butoxycarbonylphenylalanine benzyl ester → L-Phenylalanine

HRID 27806Notes

Reaction equation

HRID 27806 reaction equation
C([O:8][C:9](=[O:26])[C@H:10]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:11]C(OC(C)(C)C)=O)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])O.[Na+]>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:11][C@H:10]([C:9]([OH:26])=[O:8])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 128332N-tert-butoxycarbonylphenylalanine benzyl esterHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 6140L-PhenylalanineYield 64.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of N-t-butoxycarbonyl-L-phenylalanine benzyl ester (1 g) in methylene chloride (10 ml) is added aluminum chloride (1 g) in anisole (12 ml), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is poured into an aqueous sodium hydrogen carbonate solution and filtered to remove insoluble material. The filtrate is washed with methylene chloride, acidified to pH 2.5 with hydrochloric acid, and adsorbed on high porous polymer HP-20 (manufactured by Mitsubishi Chemical Co., Ltd.). After washing with water, the resin is washed with methanol. Concentration of the methanol eluent gives crystals of L-phenylalanine (0.3 g) melting at 270° C. Yield: 54%.

Workup

  1. filtrationfiltered
  2. customto remove insoluble material
  3. washThe filtrate is washed with methylene chloride
  4. washAfter washing with water
  5. washthe resin is washed with methanol

Sources & evidence

ORD record
ord-942e5b92eae74530b5e7f55c753590d0
Source dataset
uspto-grants-1980_09
Patent number
US04223132

Reaction notes

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