Trifluoroacetic acid → Trifluoroacetate

HRID 2112426Notes

Reaction equation

HRID 2112426 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC(=O)[NH:14][C@H:15]([C:19](=[O:21])[NH2:20])[CH2:16][C:17]#[CH:18])(C)(C)C>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[NH2:14][C@@H:15]([CH2:16][C:17]#[CH:18])[C:19]([NH2:20])=[O:21]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 45092143((S)-1-carbamoylbut-3-ynyl)carbamic acid tert-butyl ester

Product 2

HCID 84468TrifluoroacetateHCID 11194309(S)-2-aminopent-4-ynoic acid amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) was added to a solution of ((S)-1-carbamoylbut-3-ynyl)carbamic acid tert-butyl ester (138 mg, 0.65 mmol) in dichloromethane (3 ml). The reaction mixture was stirred for 1.25 h at room temperature. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (40 ml) and the solvent was removed in vacuo. The latter procedure was repeated twice to give crude trifluoroacetate salt of (S)-2-aminopent-4-ynoic acid amide, which was used for the following experiments.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (40 ml)
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c20f595147114176a85bcb11ebab6d60
Source dataset
uspto-grants-2009_04
Patent number
US07524813B2

Reaction notes

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