Benzyloxycarbonyl-L-phenylalanine → L-Phenylalanine

HRID 904112Notes

Reaction equation

HRID 904112 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 maintaining 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. temperatureWhile maintaining the nitrogen atmosphere
  2. stirringwith stirring
  3. stirringThe resulting mixture is shaken at room temperature for 4.5 to 5 hours
  4. filtrationAt the end of this period, the reaction mixture is filtered
  5. washthe residue washed
  6. customdried

Sources & evidence

ORD record
ord-9bbcc500eb934ab9a19ff1c34d767bba
Source dataset
uspto-grants-1980_10
Patent number
US04230696

Reaction notes

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