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Methanesulfonyl chloride → Methyl 2'-fluoro-2-(2-methyl-5-((methylsulfonyl)oxy)cyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662453
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HRID 1662453 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[CH:24]([CH3:25])[CH2:23][CH2:22][CH:21]1[OH:26].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[CH:21]([O:26][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:22][CH2:23][CH:24]1[CH3:25]
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참가 물질

4

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HCID 31297Methanesulfonyl chlorideHCID 57705852Methyl 2'-fluoro-2-(2-hydroxy-5-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57707123Methyl 2'-fluoro-2-(2-methyl-5-((methylsulfonyl)oxy)cyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A 250 mL round bottom flask was charged with 66.56D (mixture of diastereomers) (0.61 g, 1.7 mmol), DCM (10 mL), and TEA (0.28 mL, 2.0 mmol) and cooled to 0° C. To the cold solution was added methanesulfonyl chloride (available from Aldrich) (0.16 mL, 2.0 mmol) dropwise. The cooling bath was removed, and the mixture was stirred for 1 hour at ambient temperature. The mixture was diluted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-40% EtOAc/hexane) to afford 66.56E (mixture of diastereomers) (0.69 g, 93% yield) as a colorless oil.

후처리

  1. customThe cooling bath was removed
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography (0-40% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-1208b561eb10404da20843ead98d0adf
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030354B2

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