Methanol → HCID 57742489, compound

HRID 2266534Notes

Reaction equation

HRID 2266534 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]([CH3:30])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:10]([C:17]#[N:18])=[N:11]2.CO.O1CCCC1.[OH-].[Li+]>O>[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]([C:17]#[N:18])[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][CH:25]=1)=[C:8]2[CH3:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68782388HCID 68782388, compound

Product 1

HCID 57742489HCID 57742489, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [8-chloro-2-cyano-3-(4-methanesulfonylbenzyl)-4-methylquinolin-5-yloxy]acetic acid methyl ester (0.056 g), methanol (1.5 mL), tetrahydrofuran (1.5 mL), water (2.0 mL) and lithium hydroxide (0.60 g) was stirred at room temperature for 1 hour. The mixture was partitioned between ethyl acetate and 1.0 M aqueous hydrochloric acid. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried over sodium sulfate and the solvent removed under reduced pressure. Purification of the residue by preparative reverse-phase HPLC using a gradient over 30 minutes of acetonitrile in water gave title compound as a white solid, 0.015 g.

Workup

  1. customThe mixture was partitioned between ethyl acetate and 1.0 M aqueous hydrochloric acid
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customthe solvent removed under reduced pressure
  5. customPurification of the residue by preparative reverse-phase
  6. customover 30 minutes

Sources & evidence

ORD record
ord-cc0a20270bf94e82bc1a09c35dedc18d
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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