Lithium Hydroxide → HCID 16660417, compound

HRID 2266631Notes

Reaction equation

HRID 2266631 reaction equation
C[O:2][C:3](=[O:39])[C@@H:4]([O:6][C:7]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]2[C:8]=1[C:9]([O:35][CH:36]([F:38])[F:37])=[C:10]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:33])[NH:28][CH:29]3[CH2:32][CH2:31][CH2:30]3)=[CH:23][C:22]=1[Cl:34])[C:11]([CH2:18][CH3:19])=[N:12]2)[CH3:5].[OH-].[Li+]>O1CCCC1>[Cl:34][C:22]1[CH:23]=[C:24]([C:27](=[O:33])[NH:28][CH:29]2[CH2:30][CH2:31][CH2:32]2)[CH:25]=[CH:26][C:21]=1[CH2:20][C:10]1[C:11]([CH2:18][CH3:19])=[N:12][C:13]2[C:8]([C:9]=1[O:35][CH:36]([F:38])[F:37])=[C:7]([O:6][C@@H:4]([CH3:5])[C:3]([OH:39])=[O:2])[CH:16]=[CH:15][C:14]=2[F:17]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68784678HCID 68784678, compound

Product 1

HCID 16660417HCID 16660417, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-2-[3-(2-chloro-4-cyclobutylcarbamoylbenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]propionic acid methyl ester (0.18 g), tetrahydrofuran (5.0 mL) and 1.0 M aqueous lithium hydroxide solution (1.0 mL) was stirred at room temperature for 3 hours. 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 (9:1 to 0:1 by volume) gave title compound as a pale yellow 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 (9:1 to 0:1 by volume)

Sources & evidence

ORD record
ord-9fcab232e16d479e91eb63e8fe6d9704
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

Loading…