Trifluoroacetic acid → Caprine

HRID 374708Notes

Reaction equation

HRID 374708 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

315 mg of L-N-[(2S or R)-3-(2-hydroxyethyl)sulfonyl-2-(1-naphthylmethyl)propionyl]norleucine tert-butyl ester was dissolved in 2 ml of dry dichloromethane, and 1 ml of TFA was added thereto. The mixture was stirred at room temperature for three hours. The solvent was distilled off. The residue was recrystallized from ethyl acetate to obtain 287 mg of L-N-[(2S or R)-3-(2-hydroxyethyl)sulfonyl-2-(1naphthylmethyl)propionyl]norleucine as colorless solid.

Workup

  1. distillationThe solvent was distilled off
  2. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-edf080253a544afebe48ade810212a64
Source dataset
uspto-grants-1996_01
Patent number
US05481036

Reaction notes

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