Lithium Hydroxide → 2-(3-((7-(3-Fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)amino)phenoxy)acetic acid

HRID 1051112Notes

Reaction equation

[OH-].[Li+].[F:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH2:16][CH:17]3[NH:20][C:21]3[CH:22]=[C:23]([CH:32]=[CH:33][CH:34]=3)[O:24][CH2:25][C:26]([O:28]C(C)C)=[O:27])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH2:16][CH:17]3[NH:20][C:21]3[CH:22]=[C:23]([CH:32]=[CH:33][CH:34]=3)[O:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Aqueous lithium hydroxide (1 N, 1 mL, 1 mmol) was added to a solution of isopropyl 2-(3-((7-(3-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)amino)phenoxy)acetate (5 mg, 0.012 mmol) in THF (1 mL) in a scintillation vial. The vial was sealed and heated at 40° C. After 24 h, the reaction mixture was allowed to cool and the volatiles were concentrated in vacuo. The residue was acidified with hydrochloric acid (1 N, 1 mL), and extracted with ethyl acetate (3×2 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated to afford 3 mg (66%) of the title compound.

Workup

customThe vial was sealed
temperatureto cool
concentrationthe volatiles were concentrated in vacuo
extractionextracted with ethyl acetate (3×2 mL)
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-7ea164085da14b0eb9066a5ed4f47be2
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388153B2

Reaction notes

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