Lithium Hydroxide → HCID 16660246, compound

HRID 2266622Notes

Reaction equation

HRID 2266622 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:34][CH:35]([F:37])[F:36])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])=[CH:22][C:21]=1[Cl:33])[C:10]([CH2:17][CH3:18])=[N:11]2.O1CCCC1.[OH-].[Li+]>O>[Cl:33][C:21]1[CH:22]=[C:23]([C:26]([N:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)=[O:27])[CH:24]=[CH:25][C:20]=1[CH2:19][C:9]1[C:10]([CH2:17][CH3:18])=[N:11][C:12]2[C:7]([C:8]=1[O:34][CH:35]([F:37])[F:36])=[C:6]([O:5][CH2:4][C:3]([OH:38])=[O:2])[CH:15]=[CH:14][C:13]=2[F:16]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68781783HCID 68781783, compound

Product 1

HCID 16660246HCID 16660246, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of {3-[2-chloro-4-(pyrrolidine-1-carbonyl)benzyl]-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy}acetic acid methyl ester (0.26 g), tetrahydrofuran (5.0 mL), water (5.0 mL) and lithium hydroxide (0.040 g) was stirred at room temperature for 20 minutes. The mixture was washed with ethyl acetate and the aqueous phase acidified by the addition of 1.0 M aqueous hydrochloric acid and then extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. Purification of the residue by preparative reverse-phase HPLC, using a gradient of acetonitrile in water gave title compound as an off-white solid, 0.13 g.

Workup

  1. washThe mixture was washed with ethyl acetate
  2. additionthe aqueous phase acidified by the addition of 1.0 M aqueous hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. customthe solvent removed under reduced pressure
  6. customPurification of the residue by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-f5d396080369401d8461fc174070db6e
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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