Sodium Hydroxide → 5-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}thiophene-2-carboxylic acid
Reaction equation
[CH3:1][C:2]([CH3:25])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[S:17][C:16]([C:18]([O:20]CCCC)=[O:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].[OH-].[Na+].CO.O>C1COCC1>[CH3:3][C:2]([CH3:25])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[S:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 50 ml round bottomed flask with a stirring bar was added n-butyl 5-(4-(1,1-dimethylethoxycarbonyl)-piperazin-1-yl)-thiophene-2-carboxylate (490 mg, 1.33 mmol) and 4.2 mL of a 2.5M NaOH solution in 3:1 MeOH/H2O. THF (2 mL) was added to keep the reaction homogeneous. The reaction was stirred at room temperature and followed by HPLC. After 2 days, the reaction was concentrated in vacuo, acidified with 10% citric acid and extracted with EtOAc (3×). The combined organics were washed with water (1×), brine (1×), dried (Na2SO4), filtered, and the solvents removed in vacuo. The product was azeotroped with benzene (3×) and dried in vacuo over 2 days to yield 5-(4-(1,1-dimethylethoxycarbonyl)-piperazin-1-yl)-thiophene-2-carboxylic acid as a dark green solid.
Workup
- concentrationthe reaction was concentrated in vacuo
- extractionextracted with EtOAc (3×)
- washThe combined organics were washed with water (1×), brine (1×)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customthe solvents removed in vacuo
- customThe product was azeotroped with benzene (3×)
- customdried in vacuo over 2 days
Sources & evidence
- ORD record
- ord-e955fbbf948f49458531ffb7e5cfabd7
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05854245
Reaction notes
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