Lithium Hydroxide → [4-(4'-Trifluoromethylbiphenyl-2-carbonyl-amino)piperidin-1-yl]acetic acid

HRID 494404Notes

Reaction equation

HRID 494404 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]([C:15]2[C:16]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:14])[CH2:8][CH2:7]1)C.[OH-].[Li+]>O1CCCC1CO>[F:30][C:27]([F:28])([F:29])[C:24]1[CH:25]=[CH:26][C:21]([C:16]2[C:15]([C:13]([NH:12][CH:9]3[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:31])=[O:3])[CH2:11][CH2:10]3)=[O:14])=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57683250[4-(4'-Trifluoromethylbiphenyl-2-carbonylamino)piperidin-1-yl]acetic acid ethyl ester

Product 1

HCID 23033209[4-(4'-Trifluoromethylbiphenyl-2-carbonyl-amino)piperidin-1-yl]acetic acidYield 73.8%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

To a solution of [4-(4′-trifluoromethylbiphenyl-2-carbonylamino)piperidin-1-yl]acetic acid ethyl ester (595 mg) obtained in Example 8c) in tetrahydrofuran-methanol (1:2; 10.2 mL) was added 1M aqueous lithium hydroxide (6.8 mL), and the mixture was stirred at room temperature for 6 hours. The reaction solution was concentrated in vacuo and 2N hydrochloric acid was added to the residue to adjust the pH to about 3, thereby crystals were precipitated. The crystals were collected by filtration, washed with cold water and dried in vacuo to give the title compound (411 mg).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo and 2N hydrochloric acid
  2. additionwas added to the residue
  3. customcrystals were precipitated
  4. filtrationThe crystals were collected by filtration
  5. washwashed with cold water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4ecbb67b846e448b8662a0529cf4d0c2
Source dataset
uspto-grants-2009_05
Patent number
US07538140B2

Reaction notes

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