Dichloromethane → L-Tryptophan

HRID 1763894Notes

Reaction equation

HRID 1763894 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 Step (F) 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. stirringthe resulting mixture is shaken for 4.5 to 5 hours at room temperature
  2. filtrationAt the end of this period, the reaction mixture is filtered
  3. washthe residue washed with dimethylformamide
  4. customThe washed residue is dried

Sources & evidence

ORD record
ord-b1ce981bc2f946b997a47029dc129635
Source dataset
uspto-grants-1978_09
Patent number
US04113858

Reaction notes

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