Water → HCID 90411369, compound

HRID 1521944Notes

Reaction equation

HRID 1521944 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH:11]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)=[CH:10][C:3]=12.[OH-].[Na+].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.O>O1CCCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:31]([C:28]3[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=3)(=[O:33])=[O:32])[C:9]([CH:11]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)=[CH:10][C:3]=12

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 90413822HCID 90413822, compound

Product 1

HCID 90411369HCID 90411369, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 59C (0.5 g, 1.554 mmol) in 20 mL tetrahydrofuran, was added sodium hydroxide (0.249 g, 6.22 mmol) and the mixture was stirred at room temperature for 1 hour. p-Toluenesulfonyl chloride (0.355 g, 1.865 mmol) and benzyltriethylammonium chloride (0.018 g, 0.078 mmol) were added and the mixture was stirred for 12 hours. Water was added and the mixture was extracted with dichloromethane. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to afford the crude product which was purified by column chromatography (100-200 silica-gel in hexane and eluted with 15% ethyl acetate-hexane) to afford the title compound. LCMS: 475.1 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford the crude product which
  8. customwas purified by column chromatography (100-200 silica-gel in hexane and eluted with 15% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ddbbeb31a9014ab794e9477c333c4222
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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