Lithium Hydroxide → HCID 16660247, compound

HRID 2266624Notes

Reaction equation

HRID 2266624 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]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:28])=[CH:23][C:22]=1[Cl:34])[C:11]([CH2:18][CH3:19])=[N:12]2)[CH3:5].O1CCCC1.[OH-].[Li+]>O>[Cl:34][C:22]1[CH:23]=[C:24]([C:27]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)=[O:28])[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

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68782488HCID 68782488, compound

Product 1

HCID 16660247HCID 16660247, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (S)-2-{3-[2-chloro-4-(pyrrolidine-1-carbonyl)benzyl]-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy}propionic acid methyl ester (0.75 g), tetrahydrofuran (20 mL), water (20 mL) and lithium hydroxide (0.11 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 column chromatography on C-18 column, eluting with a mixture of water and methanol (4:1 to 0:1 by volume) gave title compound as an off-white solid, 0.20 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 column chromatography on C-18 column
  7. washeluting with a mixture of water and methanol (4:1 to 0:1 by volume)

Sources & evidence

ORD record
ord-1f65459a3f3340a6b43ff870a5f62b4c
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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