Trifluoroacetic acid → HCID 46178848, compound

HRID 1921709Notes

Reaction equation

HRID 1921709 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([N:21]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:24][N:23]=[C:22]3[S:32][C:33]([CH3:42])([CH3:41])[C:34]([O:36]C(C)(C)C)=[O:35])=[CH:13][CH:12]=2)[CH2:10][CH2:9]1>ClCCl>[CH:8]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([N:21]3[C:25]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[N:24][N:23]=[C:22]3[S:32][C:33]([CH3:42])([CH3:41])[C:34]([OH:36])=[O:35])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59223188HCID 59223188, compound

Product 1

HCID 46178848HCID 46178848, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of tert-butyl 2-(4-(4-cyclopropylnaphthalen-1-yl)-5-phenyl-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoate (25 mg, 0.051 mmol) in dichloromethane (2 mL) and the mixture stirred at room temperature for 20 hours. The mixture was then concentrated, dissolved in ethyl acetate (5 mL) and washed with water (2×5 mL). The combined aqueous layers were washed with ethyl acetate (5 mL) and the combined organic extracts were dried over sodium sulfate, filtered concentrated and purified by column chromatography (1% AcOH/40% EtOAc/hexanes) to give 2-(4-(4-cyclopropylnaphthalen-1-yl)-5-phenyl-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoic acid as a brown paste (14 mg, 64%).

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutiondissolved in ethyl acetate (5 mL)
  3. washwashed with water (2×5 mL)
  4. washThe combined aqueous layers were washed with ethyl acetate (5 mL)
  5. dry with materialthe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography (1% AcOH/40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7a258daed0a7458c90a0b53c1b0b5e75
Source dataset
uspto-grants-2012_05
Patent number
US08173690B2

Reaction notes

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