Sodium Hydroxide → HCID 58398461, compound

HRID 1879416Notes

Reaction equation

HRID 1879416 reaction equation
[F:1][CH:2]([CH3:35])[CH2:3][N:4]([S:26]([C:29]1[S:30][CH:31]=[C:32]([CH3:34])[N:33]=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][CH:17]=1.[OH-].[Na+:37]>C1COCC1.CO>[F:1][CH:2]([CH3:35])[CH2:3][N:4]([S:26]([C:29]1[S:30][CH:31]=[C:32]([CH3:34])[N:33]=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:17]=[CH:18][C:19]([C:20]([O-:22])=[O:21])=[CH:24][CH:25]=1.[Na+:37]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58398472methyl 4-{[(6-{(2-fluoropropyl)[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate

Product 1

HCID 58398461HCID 58398461, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

351 mg of methyl 4-{[(6-{(2-fluoropropyl)[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate was dissolved in 5.00 mL of THF and 5.00 mL of methanol, and 2.03 mL of a 1 M aqueous sodium hydroxide solution was added thereto, followed by stirring at 50° C. for 4 hours. The reaction liquid was concentrated under reduced pressure, to the obtained residue were added a 5% w/v aqueous citric acid solution and chloroform, and the organic layer was separated using a Phase Separate-filter manufactured by Isotute, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was dissolved in 5.00 mL of ethanol, and 0.765 mL of an aqueous sodium hydroxide solution was added thereto, followed by concentration under reduced pressure. The obtained crude product was crystallized by the addition of isopropanol/ethanol, collected by filtration, and dried under reduced pressure to obtain 268 mg of sodium 4-{[(6-{(2-fluoropropyl)[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure, to the obtained residue
  3. additionwere added a 5% w/v aqueous citric acid solution and chloroform
  4. customthe organic layer was separated
  5. filtrationSeparate-filter
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. dissolutionthe obtained residue was dissolved in 5.00 mL of ethanol
  9. addition0.765 mL of an aqueous sodium hydroxide solution was added
  10. concentrationfollowed by concentration under reduced pressure
  11. customThe obtained crude product
  12. customwas crystallized by the addition of isopropanol/ethanol
  13. filtrationcollected by filtration
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-6562713d499948788947e8858646aba2
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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