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

HRID 849889Notes

Reaction equation

HRID 849889 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:20](=[O:48])[NH:21][C@@H:22]([C:34]1[S:35][C:36]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:37]([C:39](=[O:41])[NH2:40])[N:38]=1)[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@H:8]([CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[C:20]([NH:21][C@@H:22]([C:34]1[S:35][C:36]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:37]([C:39]([NH2:40])=[O:41])[N:38]=1)[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)=[O:48]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53997581((1R)-1-((1R)-1-(4-Carbamoyl-5-phenyl-1,3-thiazol-2-yl)-2-(2-naphthyl)ethylcarbamoyl)-2-(2-naphthyl)ethyl)carbamic acid tert-butylester

Product 1

HCID 542665712-((1R)-1-((2R)-2-amino-3-(2-naphthyl)propionylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amideYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((1R)-1-((1R)-1-(4-Carbamoyl-5-phenyl-1,3-thiazol-2-yl)-2-(2-naphthyl)ethylcarbamoyl)-2-(2-naphthyl)ethyl)carbamic acid tert-butylester (0.22 g; 0.328 mmol) was dissolved in methylene chloride (2.5 ml) and trifluoroacetic acid (2.5 ml) was added. The reaction mixture was stirred 1 h at room temperature and the solvent was removed in vacuo. The residue was dissolved in methylene chloride and evaporated (2×5 ml). The residue was dissolved in methylene chloride (10 ml) and washed with sodium hydrogencarbonate (satd; 10 ml), water (10 ml) and dried (magnesium sulfate). The solvent was removed in vacuo to afford 0.155 g of 2-((1R)-1-((2R)-2-amino-3-(2-naphthyl)propionylamino)-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 (2×5 ml)
  4. dissolutionThe residue was dissolved in methylene chloride (10 ml)
  5. washwashed with sodium hydrogencarbonate (satd; 10 ml), water (10 ml)
  6. dry with materialdried (magnesium sulfate)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c2e465fe8942436e84b2e4c83cbae898
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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