4-Fluorobenzenesulfonyl chloride → HCID 178473725, compound

HRID 849423Notes

Reaction equation

HRID 849423 reaction equation
Cl.Cl.Cl.[NH:4]1[CH:8]=[C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]4[CH:22]=N[CH:24]=[CH:25][CH:26]=4)=[CH:20][C:15]=3[CH2:14][N:13]([C:27](=[O:32])[C:28](F)(F)F)[CH:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:11]2)[N:6]=[CH:5]1.[C:40]([O-])(O)=O.[Na+].FC1C=CC(S([Cl:55])(=O)=O)=CC=1.[OH-].[Na+].[NH4+].[OH-]>C(Cl)Cl.CO>[ClH:55].[C:27]([N:13]1[CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:22]=[CH:40][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:16]=2[N:10]([CH2:9][C:7]2[N:6]=[CH:5][NH:4][CH:8]=2)[CH2:11][C@H:12]1[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:32])[CH3:28]

Participants

8

Reactant 5

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 516892Sodium BicarbonateHCID 178478619HCID 178478619, compound

Product 1

HCID 178473725HCID 178473725, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Compound B (150 mg, 0.6 mmol) in methylene chloride with saturated NaHCO3 solution was added 4-fluorobenzenesulfonyl chloride (300 mg, 1.55 mmol). The mixture was stirred at room temperature for 18 h and diluted with methanol. 10 N NaOH was added and the mixture was stirred for 2 h. Concentrated NH4OH was added and the mixture was stirred for 18 h and concentrated in vacuo. The residue was partitioned between ethyl acetate and saturated NaHCO3. The organic layer was separated, dried over MgSO4, and concentrated in vacuo. The residue was purified by chromatography (1:4, ethyl acetate and hexanes) to give Compound C as an oil (120 mg, 50%).

Workup

  1. stirringthe mixture was stirred for 2 h
  2. stirringthe mixture was stirred for 18 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and saturated NaHCO3
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography (1:4, ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-67a0bf240dfb49b39fda6d5c365abd66
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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