Lithium Hydroxide → HCID 16660416, compound

HRID 2266629Notes

Reaction equation

HRID 2266629 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](=[O:32])[NH:27][CH:28]3[CH2:31][CH2:30][CH2:29]3)=[CH:22][C:21]=1[Cl:33])[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[Cl:33][C:21]1[CH:22]=[C:23]([C:26](=[O:32])[NH:27][CH:28]2[CH2:31][CH2:30][CH2:29]2)[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

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68784786HCID 68784786, compound

Product 1

HCID 16660416HCID 16660416, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(2-chloro-4-cyclobutylcarbamoylbenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.23 g), tetrahydrofuran (5.0 mL) and 1.0 M aqueous lithium hydroxide solution (1.2 mL) was stirred at room temperature for 30 minutes. The mixture was concentrated under reduced pressure, acidified by the addition of sodium dihydrogenphosphate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. Purification of the residue by column chromatography on C-18 column, eluting with a mixture of water and methanol gave title compound as an off-white solid, 0.13 g.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionacidified by the addition of sodium dihydrogenphosphate
  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 column chromatography on C-18 column
  7. washeluting with a mixture of water and methanol

Sources & evidence

ORD record
ord-5d847f0bf76845679e5e592c8df0de16
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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