Sulfuric Acid → HCID 22279875, compound

HRID 1063449Notes

Reaction equation

HRID 1063449 reaction equation
[ClH:1].[NH2:2][C:3]([CH3:24])([CH2:6][CH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=1)[CH2:4][OH:5].S(=O)(=O)(O)[OH:26].[OH-].[Na+]>CO>[ClH:1].[NH2:2][C:3]([CH3:24])([CH2:6][CH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[O:26])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:12]=1)[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 22279832HCID 22279832, compound

Product 1

HCID 22279875HCID 22279875, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Amino-2-methyl-4-[4-(5-phenylpent-1-ynyl)thiophen-2-yl]butan-1-ol hydrochloride (178 mg, 0.49 mmol) obtained in Example 26 (i) was dissolved in methanol (2 ml), and 6N sulfuric acid (2 ml) was added thereto followed by heating under reflux for 4 hours. After the reaction solution was made alkaline with a 1N aqueous sodium hydroxide solution, the resulting solution was extracted with dichloromethane. The dichloromethane layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The residue was dissolved in 1,4-dioxane (2 ml), and the dioxane solution of 4N hydrochloric acid was added thereto in an ice bath, and then the solvent was evaporated under reduced pressure. The obtained white solid was washed with ether, and dried to give the title compound (100 mg, 53% yield).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. extractionthe resulting solution was extracted with dichloromethane
  4. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. dissolutionThe residue was dissolved in 1,4-dioxane (2 ml)
  7. additionthe dioxane solution of 4N hydrochloric acid was added
  8. customin an ice bath, and then the solvent was evaporated under reduced pressure
  9. washThe obtained white solid was washed with ether
  10. customdried

Sources & evidence

ORD record
ord-121632e2208540f28054a02561c19fcf
Source dataset
uspto-grants-2005_11
Patent number
US06964976B2

Reaction notes

Loading…