Hydrochloric Acid → HCID 70655426, compound

HRID 1972513Notes

Reaction equation

HRID 1972513 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C@@H:11]([CH2:28][C:29]#N)[CH2:10]1)(=[O:8])=[O:7].[OH-:31].[Na+].[OH2:33].CCO.[ClH:37]>O>[ClH:37].[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:27])([CH3:26])[C:22]([F:23])([F:25])[F:24])=[CH:17][CH:16]=2)[C@@H:11]([CH2:28][C:29]([OH:33])=[O:31])[CH2:10]1)(=[O:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19096565Water ethanolHCID 66582854HCID 66582854, compound

Product 1

HCID 70655426HCID 70655426, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-((2S)-4-(thiophen-2-ylsulfonyl)-1-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)piperazin-2-yl)acetonitrile (1.10 g, 2.40 mmol) and 5 M NaOH (3 mL) in 2:1 water-EtOH (10 mL) was heated to 150° C. and stirred for 1 h. Afterwards, the mixture was diluted with water (30 mL) and then neutralized with concentrated HCl to a pH of about 2 to 3. The aqueous solution was extracted with 3×EtOAc (20 mL). The organic layer was dried over is MgSO4, filtered, and concentrated. The crude product was then dissolved in 1 N NaOH. The basic solution was extracted with 2×EtOAc. The basic aqueous solution was then neutralized with concentrated HCl and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was dissolved in EtOAc (30 mL) and the solution was slowly acidified with 1 N HCl in diethyl ether. The resulting precipitate was collected and dried to give ((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)acetic acid hydrochloride (0.655 g).

Workup

  1. extractionThe aqueous solution was extracted with 3×EtOAc (20 mL)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe crude product was then dissolved in 1 N NaOH
  6. extractionThe basic solution was extracted with 2×EtOAc
  7. extractionextracted with EtOAc
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. dissolutionThe residue was dissolved in EtOAc (30 mL)
  12. customThe resulting precipitate was collected
  13. customdried

Sources & evidence

ORD record
ord-afb63649953f4bd1900d02e0a1fb27fe
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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