Benzyloxycarbonyl-L-phenylalanine → L-Phenylalanine

HRID 1763895Notes

Reaction equation

HRID 1763895 reaction equation
C([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(OCC1C=CC=CC=1)=O>C(Cl)Cl>[NH2:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 1

HCID 70878Benzyloxycarbonyl-L-phenylalanine

Product 1

HCID 6140L-Phenylalanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

While maintaning the nitrogen atmosphere, the product of Step (J) above is admixed with 3 fold molar excess of carbobenzoxy-L-phenylalanine [Boc-L-phenylalanine, Peninsula, supra.] dissolved in methylene chloride. The resulting mixture is shaken and after about 10 minutes, 3 fold molar excess of N,N-dicyclohexylcarbodiimide in 15 ml of methylene chloride is added with stirring. The resulting mixture is shaken at room temperature for 4.5 to 5 hours. At the end of this period, the reaction mixture is filtered and the residue washed and dried.

Workup

  1. stirringwith stirring
  2. stirringThe resulting mixture is shaken at room temperature for 4.5 to 5 hours
  3. filtrationAt the end of this period, the reaction mixture is filtered
  4. washthe residue washed
  5. customdried

Sources & evidence

ORD record
ord-7ac26b1105d94ffbbc3115140b491cfa
Source dataset
uspto-grants-1978_09
Patent number
US04113858

Reaction notes

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