Hydrochloric Acid → (S)-2-[2-cyclopropyl-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]propionic acid

HRID 1922162Notes

Reaction equation

HRID 1922162 reaction equation
C[O:2][C:3](=[O:34])[C@@H:4]([O:6][C:7]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]2[C:8]=1[C:9]([CH3:33])=[C:10]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[CH:31][CH:30]=[N:29]3)=[CH:24][CH:23]=1)[C:11]([CH:18]1[CH2:20][CH2:19]1)=[N:12]2)[CH3:5].[OH-].[Li+].Cl>O1CCCC1.O>[CH:18]1([C:11]2[C:10]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([N:28]4[CH:32]=[CH:31][CH:30]=[N:29]4)=[CH:26][CH:27]=3)=[C:9]([CH3:33])[C:8]3[C:13](=[C:14]([F:17])[CH:15]=[CH:16][C:7]=3[O:6][C@@H:4]([CH3:5])[C:3]([OH:34])=[O:2])[N:12]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67457321(S)-2-[2-cyclopropyl-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]propionic acid methyl ester

Product 1

HCID 25097871(S)-2-[2-cyclopropyl-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]propionic acidYield 71.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-2-[2-cyclopropyl-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]propionic acid methyl ester (0.033 g) in tetrahydrofuran (0.18 mL) and water (0.18 mL) was treated with lithium hydroxide (0.018 g), and the resulting mixture was stirred at room temperature for 4 hours. The mixture was cooled to 0° C., diluted with water (10 mL) and acidified by the addition of 1.0 M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the combined extracts were dried over magnesium sulfate and concentrated under reduced pressure to afford title compound as a yellow solid (0.023 g).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ea4855702cf4a9b8f5f33335b35939a
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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