Trifluoroacetic acid → 2-((1R)-1-amino-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amide

HRID 1701073Notes

Reaction equation

HRID 1701073 reaction equation
C(OC([NH:8][C@@H:9]([C:21]1[S:22][C:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:24]([C:26]([NH2:28])=[O:27])[N:25]=1)[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)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@@H:9]([C:21]1[S:22][C:23]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:24]([C:26]([NH2:28])=[O:27])[N:25]=1)[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

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 543097762-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amide

Product 1

HCID 540396812-((1R)-1-amino-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amideYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-((1R)-1-(tert-Butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amide (0.155 g; 0.327 mmol) was dissolved in methylene chloride (4 ml) and trifluoroacetic acid (4 ml) was added. The reaction mixture was stirred 1 hour at room temperature and the solvent was removed in vacuo. The residue was dissolved in methylene chloride and evaporated (2×2 ml). The residue was dissolved in diethyl ether (2 ml). Hydrochloric acid (1 N; 3 ml) and methanol (10 ml) were added. The solvent was removed in vacuo to afford 0.106 g of 2-((1R)-1-amino-2-(2-naphthyl)-ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amide.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. customevaporated (2×2 ml)
  4. dissolutionThe residue was dissolved in diethyl ether (2 ml)
  5. additionHydrochloric acid (1 N; 3 ml) and methanol (10 ml) were added
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4041a53d00f245a5a3b6d4246c9de74e
Source dataset
uspto-grants-2002_02
Patent number
US06350767B1

Reaction notes

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