Lithium Hydroxide → 2-({2-[4-(2-{Ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]ethyl}thio)benzoic acid
Reaction equation
[CH2:1]([N:3]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1)[C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15][C:16]2[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20]C)=[O:19])=[CH:9][CH:8]=1)[CH3:2].[OH-].[Li+]>C(#N)C.O>[CH2:1]([N:3]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([F:36])([F:35])[F:37])=[CH:32][CH:33]=1)[C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][S:15][C:16]2[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([OH:20])=[O:19])=[CH:11][CH:12]=1)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 2-({2-[4-(2-{ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-ethyl}thio)benzoate (0.085 g, 0.160 mmol) was dissolved in a mixture of acetonitrile/water (1/1, 4 ml), then lithium hydroxide (0.008 g, 0.320 mmol) was added. The reaction was performed in an single node microwave oven (5 min, 150 deg). Work-up by removing the solvent by evaporation and addition of HCl (2 ml, 1 M). The water phase was extracted with two portions of EtOAc (20 ml), the organic phase was dried (MgSO4) and the solvent was removed by evaporation and gave 0.07773 g of 2-({2-[4-(2-{ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]ethyl}thio)benzoic acid (yield 93.0%).
Workup
- customThe reaction was performed in an single node microwave oven
- custom(5 min, 150 deg)
- customby removing the solvent
- customby evaporation and addition of HCl (2 ml, 1 M)
- extractionThe water phase was extracted with two portions of EtOAc (20 ml)
- dry with materialthe organic phase was dried (MgSO4)
- customthe solvent was removed by evaporation
Sources & evidence
- ORD record
- ord-bd511eed46bd41f7a44e8757f52301ad
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351858B2
Reaction notes
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