HCID 67023968, compound → HCID 67024027, compound

HRID 450734Notes

Reaction equation

HRID 450734 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH:17]([CH2:23][NH:24]C(=O)CC)[CH2:18]3)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>C(O)CCC>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH:17]([CH2:23][NH2:24])[CH2:18]3)(=[O:12])=[O:11])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 67023968HCID 67023968, compound

Product 1

HCID 67024027HCID 67024027, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

N-[4-(4-Isopropyl-benzenesulfonylamino)-indan-2-ylmethyl]-propionamide (1.00 g, 2.50 mmol, synthesized as described in Example 8) was dissolved in 25 mL of n-butanol and 10 mL of concentrated (6N) hydrochloric acid was added. The resulting mixture was stirred at reflux for 5 h. The solution was cooled, added to water and extracted with ethyl acetate. The aqueous solution was treated with NaOH (2N) and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and the filtrate was evaporated in vacuo to give product as a white solid which was further purified by column chromatography using (dichloromethane-MeOH, 5-50%) to give a yellow oil (160 mg, 18%).

Workup

  1. concentration10 mL of concentrated (6N) hydrochloric acid
  2. additionwas added
  3. temperatureat reflux for 5 h
  4. temperatureThe solution was cooled
  5. additionadded to water
  6. extractionextracted with ethyl acetate
  7. additionThe aqueous solution was treated with NaOH (2N)
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic phase was dried over MgSO4
  10. filtrationfiltered
  11. customthe filtrate was evaporated in vacuo
  12. customto give product as a white solid which
  13. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-34df4adf6fa948298183207e913998cd
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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