Trifluoroacetic acid → Caprine

HRID 2255777Notes

Reaction equation

HRID 2255777 reaction equation
C([O:5][C:6](=[O:13])[C@H:7]([CH2:9][CH2:10][CH2:11][CH3:12])[NH2:8])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C@H:7]([C:6]([OH:13])=[O:5])[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12451446tert-butyl (2S)-2-aminohexanoate

Product 1

HCID 21236Caprine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

109 mg of L-N-[(2S or R)-3-(2-hydroxyethyl)sulfinyl-2-(1-naphthylmethyl)propionyl]norleucine tert-butyl ester was dissolved in 0.4 ml of dry dichloromethane, and 0.4 ml of TFA was added thereto. The mixture was stirred at room temperature for 2.5 hours. Then, the solvent was distilled off. To the residue, benzene was added, and the mixture was concentrated under reduced pressure. This operation was repeated to obtain 94.8 mg of L-N-[(2S or R)-3-(2-hydroxyethyl)sulfinyl-2-(1-naphthylmethyl)propionyl]norleucine as colorless solid.

Workup

  1. distillationThen, the solvent was distilled off
  2. additionTo the residue, benzene was added
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-07f227f2b3ff42f7b841c3e49f287d2d
Source dataset
uspto-grants-1993_08
Patent number
US05240924

Reaction notes

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