Potassium → (2R,4R)-2-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)-4-hydroxy-N-((S)-7-(trifluoromethyl)chroman-4-yl)pyrrolidine-1-carboxamide

HRID 2063472Notes

Reaction equation

HRID 2063472 reaction equation
C([O:4][C@@H:5]1[CH2:9][C@H:8]([C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[C:13]([CH3:23])=[N:12][N:11]=2)[N:7]([C:24](=[O:40])[NH:25][C@@H:26]2[C:35]3[C:30](=[CH:31][C:32]([C:36]([F:39])([F:38])[F:37])=[CH:33][CH:34]=3)[O:29][CH2:28][CH2:27]2)[CH2:6]1)(=O)C.[K]>CO>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:14]2[C:13]([CH3:23])=[N:12][N:11]=[C:10]2[C@H:8]2[CH2:9][C@@H:5]([OH:4])[CH2:6][N:7]2[C:24]([NH:25][C@@H:26]2[C:35]3[C:30](=[CH:31][C:32]([C:36]([F:37])([F:39])[F:38])=[CH:33][CH:34]=3)[O:29][CH2:28][CH2:27]2)=[O:40])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 5462222PotassiumHCID 68811435(3R,5R)-1-(((S)-7-(trifluoromethyl)chroman-4-yl)carbamoyl)-5-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)pyrrolidin-3-yl acetate

Product 1

HCID 57650462(2R,4R)-2-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)-4-hydroxy-N-((S)-7-(trifluoromethyl)chroman-4-yl)pyrrolidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude (3R,5R)-1-(((S)-7-(trifluoromethyl)chroman-4-yl)carbamoyl)-5-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)pyrrolidin-3-yl acetate from Step F (120 mg, 0.21 mmol) in aqueous MeOH (2.0 ml, 1:1 water:MeOH) was added potassium carbonated (116 mg, 0.84 mmol). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated and the residue dissolved in EtOAc, washed with 1N HCl and then concentrated. Preparative HPLC purification provided the desired compound as a white fluffy solid (47 mg, 72% over 3 steps).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with 1N HCl
  4. concentrationconcentrated
  5. customPreparative HPLC purification

Sources & evidence

ORD record
ord-33e8170ede2b47aabe2b15ed50f658d3
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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