4-Fluorobenzenesulfonyl chloride → HCID 178473725, 화합물

HRID 849423노트

반응식

HRID 849423 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

HCID 178473725HCID 178473725, 화합물수율 50%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-67a0bf240dfb49b39fda6d5c365abd66
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011029

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