Dichloromethane → L-Tryptophan

HRID 904114Notes

Reaction equation

HRID 904114 reaction equation
C([NH:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(OC(C)(C)C)=O.C(Cl)Cl>CN(C)C=O>[NH2:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 83169N-tert-Butoxycarbonyl-L-tryptophan

Product 1

HCID 6305L-Tryptophan

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

While maintaining the nitrogen gas atmosphere, 3 fold molar excess of Boc-L-Tryptophan (Peninsula, supra.) dissolved in dimethylformamide and adjusted to 15 ml. with the addition of methylene chloride is added to the product of the previous step above and the resulting mixture shaken. After about 10 minutes, 3 fold molar excess of N,N-dicyclohexylcarbodiimide is added and the resulting mixture is shaken for 4.5 to 5 hours at room temperature. At the end of this period, the reaction mixture is filtered and the residue washed with dimethylformamide. The washed residue is dried.

Workup

  1. additionis added to the product of the previous step above
  2. stirringthe resulting mixture is shaken for 4.5 to 5 hours at room temperature
  3. filtrationAt the end of this period, the reaction mixture is filtered
  4. washthe residue washed with dimethylformamide
  5. customThe washed residue is dried

Sources & evidence

ORD record
ord-7f39c73fa4024954b2e53b1d688e1697
Source dataset
uspto-grants-1980_10
Patent number
US04230696

Reaction notes

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