Trifluoroacetic acid → Caprine

HRID 893150Notes

Reaction equation

HRID 893150 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-6e169b363c3e4d2abbf6c8a9239b98c0
Source dataset
uspto-grants-1992_06
Patent number
US05122523

Reaction notes

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