Hydrochloric Acid → HCID 57742488, compound

HRID 2266515Notes

Reaction equation

HRID 2266515 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.CO.[OH-].[Li+].Cl>O.O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:31])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH2:17][CH3:18])[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)=[C:8]2[O:27][CH:28]([F:30])[F:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68782512HCID 68782512, compound

Product 1

HCID 57742488HCID 57742488, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [8-chloro-4-difluoromethoxy-2-ethyl-3-(4-fluorobenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.060 g), methanol (1.5 mL), tetrahydrofuran (1.5 mL), water (1.0 mL) and lithium hydroxide (0.01 g) was stirred at room temperature for 1 hour. The mixture was acidified by the addition of 1.0 M aqueous hydrochloric acid, extracted with ethyl acetate and the combined extracts dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by preparative reverse-phase HPLC using a gradient of acetonitrile in water gave title compound as a yellow solid, 0.022 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined extracts dried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure and purification of the residue by preparative reverse-phase

Sources & evidence

ORD record
ord-fbbc76b805d2400299aeb8291426c0a1
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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