Sodium Hydroxide → HCID 58398428, compound

HRID 1879417Notes

Reaction equation

HRID 1879417 reaction equation
[F:1][CH:2]([CH3:35])[CH2:3][N:4]([S:26]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27])[C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[O:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][N:17]=1.[OH-].[Na+]>C1COCC1.CO>[F:1][CH:2]([CH3:35])[CH2:3][N:4]([S:26]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27])[C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[O:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][N:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58398381HCID 58398381, compound

Product 1

HCID 58398428HCID 58398428, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

148 mg of methyl 6-[({6-[(2-fluoropropyl)(pyridin-3-ylsulfonyl)amino]-2,3-dihydro-1H-inden-5-yl}oxy)methyl]nicotinate was dissolved in 3.00 mL of THF and 1.50 mL of methanol, and 1.50 mL of a 1 M aqueous sodium hydroxide solution was added thereto, followed by stirring overnight at room temperature. The reaction liquid was concentrated under reduced pressure, and to the obtained residue was added a 5% w/v aqueous citric acid solution, followed by extraction with chloroform. The organic layer was concentrated under reduced pressure, and the obtained crude product was crystallized by the addition of isopropanol/diisopropyl ether, collected by filtration, and dried under reduced pressure to obtain 79 mg of 6-[({6-[(2-fluoropropyl)(pyridin-3-ylsulfonyl)amino]-2,3-dihydro-1H-inden-5-yl}oxy)methyl]nicotinic acid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additionto the obtained residue was added a 5% w/v aqueous citric acid solution
  4. extractionfollowed by extraction with chloroform
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe obtained crude product
  7. customwas crystallized by the addition of isopropanol/diisopropyl ether
  8. filtrationcollected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-57b8ff88f13f4c6d84db3a008c2acec1
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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