Lithium Hydroxide → 2-(3-(6-Hexyl-1-naphthamido)phenoxy)acetic acid
Reaction equation
[OH-].[Li+].[CH2:3]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=1)[O:25][CH2:26][C:27]([O:29]C(C)C)=[O:28])=[O:20])=[CH:14][CH:13]=[CH:12]2)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C1COCC1>[CH2:3]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=1)[O:25][CH2:26][C:27]([OH:29])=[O:28])=[O:20])=[CH:14][CH:13]=[CH:12]2)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Aqueous 1 N lithium hydroxide (0.5 mL, 0.5 mmol) was added to a solution of isopropyl 2-(3-(6-hexyl-1-naphthamido)phenoxy)acetate (44 mg, 0.98 mmol) in THF (0.5 mL) in a scintillation vial. The vial was sealed and heated at 60° C. After 40 h, the reaction mixture was allowed to cool and the volatiles were evaporated under a stream of nitrogen. The residue was diluted with water (2 mL), acidified with 1 N aqueous HCl (2 mL) and extracted with EtOAc (3×20 mL). The combined organic phase was washed with brine (10 mL), then dried (Na2SO4), filtered and concentrated in vacuo to afford 36 mg (90%) of the title compound.
Workup
- customThe vial was sealed
- temperatureto cool
- customthe volatiles were evaporated under a stream of nitrogen
- additionThe residue was diluted with water (2 mL)
- extractionextracted with EtOAc (3×20 mL)
- washThe combined organic phase was washed with brine (10 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ea71e81e2daa47a3b3527e2453182faf
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633220B2
Reaction notes
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