Sodium Hydroxide → HCID 131728751, compound

HRID 604047Notes

Reaction equation

HRID 604047 reaction equation
[F:1][C:2]([F:50])([F:49])[C:3]1[CH:4]=[C:5]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:6][N:7]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1[N:34]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:35][CH3:36])[C:8]1[N:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=[O:21])[CH2:16][CH2:15]2)=[CH:10][N:9]=1.[OH-].[Na+:52]>C(O)C>[Na+:52].[F:50][C:2]([F:1])([F:49])[C:3]1[CH:4]=[C:5]([CH:42]=[C:43]([C:45]([F:46])([F:48])[F:47])[CH:44]=1)[CH2:6][N:7]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1[N:34]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:35][CH3:36])[C:8]1[N:13]=[CH:12][C:11]([N:14]2[CH2:15][CH2:16][CH:17]([C:20]([O-:22])=[O:21])[CH2:18][CH2:19]2)=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 87263186HCID 87263186, compound

Product 1

HCID 131728751HCID 131728751, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-{(3,5-Bis-trifluoromethyl-benzyl)-[2-(ethoxycarbonyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yl)-ethyl piperidine-4-carboxylate (70 mg) is dissolved in ethanol (4 ml), and thereto is added 1N-aqueous sodium hydroxide solution (1 ml) and the mixture is stirred at room temperature for 2 hours. To the reaction solution are added a 1N-hydrochloric acid and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→9:1) to give 1-(2-{(3,5-bis-trifluoromethyl-benzyl)-[2-(ethoxycarbonyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yl)-piperidine-4-carboxylic acid (44 mg). The resulting 1-(2-{(3,5-bis-trifluoromethyl-benzyl)-[2-(ethoxycarbonyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yl)-piperidine-4-carboxylic acid (44 mg) is dissolved in ethanol (1 ml), and thereto is added 1N-aqueous sodium hydroxide solution (44 μl), and then the mixture is concentrated under reduced pressure to give 1-(2-{(3,5-bis-trifluoromethyl-benzyl)-[2-(ethoxycarbonyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yl)-piperidine-4-carboxylic acid sodium salt (45 mg). MS (m/z): 720 [M−Na]−

Workup

  1. concentrationthe mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-cc398cc3cb18435c82caf20bb24116e8
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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