Tetrahydrofuran → 1-(1-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)piperidin-4-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

HRID 2196545Notes

Reaction equation

HRID 2196545 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:31])[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][C:19]([C:27]([F:30])([F:29])[F:28])=[N:18]2)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C1COCC1>C(O)C>[C:1]([O:5][C:6]([N:8]([CH3:31])[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]([C:27]([F:28])([F:30])[F:29])=[N:18]2)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59843232ethyl 1-(1-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)piperidin-4-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 598432141-(1-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)piperidin-4-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 95 (1.09 g, 2.43 mmol) in ethanol (8.1 ml) was added a solution of NaOH (2.43 ml, 2N, 4.86 mmol) followed by THF (1.6 ml). After stirring at room temperature for 1 h, the mixture was taken to dryness and crude 96 was used as is for the next step. LRMS (ESI): calc. 420.4; found 421.3 (MH)+.

Sources & evidence

ORD record
ord-a688a85d679e452daeef0113dc490586
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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