Sodium Hydroxide → N-[2-(4-Carboxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([OH:26])[C:17]2[N:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[S:20][CH:21]=2)[CH3:13])=[CH:7][CH:6]=1)([O:3]C)=[O:2].[OH-].[Na+]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([OH:26])[C:17]2[N:18]=[C:19]([C:22]([F:24])([F:23])[F:25])[S:20][CH:21]=2)[CH3:13])=[CH:7][CH:6]=1)([OH:3])=[O:2]Participants
3
Procedure
Prepared analogously to Example 2 by reaction of N-[2-(4-carbomethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine with 1N sodium hydroxide solution. After neutralisation with hydrochloric acid, the mixture is evaporated to dryness and the residue is treated with a mixture of ethyl acetate/ethanol=6:1. The extract is evaporated to dryness and the residue is triturated with 5 ml of water. The water is decanted off and the remaining residue is taken up in methanol, the solution is evaporated to dryness, and the residue is triturated with ether and filtered off with suction.
Workup
- customAfter neutralisation with hydrochloric acid, the mixture is evaporated to dryness
- additionthe residue is treated with a mixture of ethyl acetate/ethanol=6:1
- customThe extract is evaporated to dryness
- customthe residue is triturated with 5 ml of water
- customThe water is decanted off
- customthe solution is evaporated to dryness
- customthe residue is triturated with ether
- filtrationfiltered off with suction
Sources & evidence
- ORD record
- ord-7ecb5f105ad54bdcbe7d11c2410e15a1
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04886814
Reaction notes
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