Sodium Hydroxide → HCID 44601271, compound

HRID 1177477Notes

Reaction equation

HRID 1177477 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[OH-].[Na+]>C1COCC1.C([O-])(=O)C.[Na+]>[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67111689HCID 67111689, compound

Product 1

HCID 44601271HCID 44601271, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 517045Sodium AcetateSolvent

Procedure

To a slurry of methyl 3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)propanoate (0.114 g, 0.26 mmol) in 3 mL THF/1 mL water was added sodium hydroxide (0.53 mL, 0.53 mmol). The reaction mixture became light yellow and was still heterogeneous. After stirring overnight, the slightly milky solution was treated with a stream of nitrogen to remove the THF, then 0.53 mL 1N HCl to neutralize base, at which point a white precipitate formed, and diluted with 3 mL 3M pH 4.8 sodium acetate buffer. The reaction mixture was filtered and the solid rinsed with water and MeOH. The solid was collected and dried in vacuo to give 3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)propanoic acid as a white solid. MS (ESI) m/z; calculated: 418.1; Observed: 419.1 (M++1).

Workup

  1. additionthe slightly milky solution was treated with a stream of nitrogen
  2. customto remove the THF
  3. customat which point a white precipitate formed
  4. filtrationThe reaction mixture was filtered
  5. washthe solid rinsed with water and MeOH
  6. customThe solid was collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b16568c0391b420aae435734738d4b2e
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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