Trifluoroacetic acid → [(5-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}pyridin-3-yl)oxy]acetic acid

HRID 534901Notes

Reaction equation

HRID 534901 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:20]=[C:21]([O:25][CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[CH:22]=[N:23][CH:24]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.[OH-].[Na+]>O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:20]=[C:21]([O:25][CH2:26][C:27]([OH:29])=[O:28])[CH:22]=[N:23][CH:24]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 66751333tert-Butyl [(5-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}pyridin-3-yl)oxy]acetate

Product 1

HCID 66792761[(5-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}pyridin-3-yl)oxy]acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tert-butyl [(5-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}pyridin-3-yl)oxy]acetate obtained in Example 35 (500 mg) and trifluoroacetic acid (7 mL) was stirred at room temperature for 3 h. Water was added to the reaction solution, and subsequently 1 M sodium hydroxide solution was added to the mixture to pH 5-6. The resulting precipitate was collected and dried under reduced pressure to provide the title compound (405 mg, 93%) as crystals.

Workup

  1. additionwas added to the mixture to pH 5-6
  2. customThe resulting precipitate was collected
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-2ec8879cae6a42419f6b0d4723a846d1
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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