Trifluoroacetic acid → HCID 54560552, compound

HRID 849855Notes

Reaction equation

HRID 849855 reaction equation
C(O[C:6](=O)[N:7]([C@@H:9]([C:21](=[O:40])[N:22]([C@@H:24]([C:32]1[O:33][C:34]([C:37](=[O:39])[NH2:38])=[N:35][N:36]=1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:23])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:23][N:22]([C:21](=[O:40])[C@H:9]([NH:7][CH3:6])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[C@@H:24]([C:32]1[O:33][C:34]([C:37]([NH2:38])=[O:39])=[N:35][N:36]=1)[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53973617HCID 53973617, compound

Product 1

HCID 54560552HCID 54560552, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

((1R)-1-(((1R)-1-(5-Carbamoyl-[1,3,4]oxadiazol-2-yl)-2-phenylethyl)methylcarbamoyl)-2-(2-naphthyl)ethyl)methylcarbamic acid tert-butylester (300 mg, 0.55 mmol) was dissolved in dichloromethane (3 ml) and cooled to 0° C. Trifluoroacetic acid (3 ml) was added dropwise. The solution was stirred for 5 min at 0° C. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (5 ml), and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (5 ml), and the solvent was removed in vacuo. The residue was dissolved in 3M hydrogen chloride in ethyl acetate (5 ml), and the solvent was removed in vacuo. The residue was dissolved in 3M hydrogen chloride in ethyl acetate (5 ml), and the solvent was removed in vacuo to give 238 mg of crude 5-((1R)-1-(methyl((2R)-2-methylamino-3-(2-naphthyl)propionyl)amino)-2-phenylethyl)-[1,3,4]oxadiazol-2-carboxylic acid amide, which was used for the further synthesis.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (5 ml)
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (5 ml)
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in 3M hydrogen chloride in ethyl acetate (5 ml)
  7. customthe solvent was removed in vacuo
  8. dissolutionThe residue was dissolved in 3M hydrogen chloride in ethyl acetate (5 ml)
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1a0e0b96d2834ff48c770373a7e6ccd3
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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