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Sodium Thiosulfate → N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylsulfonyl)phenyl)methanesulfonamide

HRID 1051830
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HRID 1051830 반응식
[Si:1]([O:18][CH2:19][C:20]1[C:25](SC)=[CH:24][C:23]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[C:22]([I:33])[CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:34]1C=C(Cl)C=C(C(OO)=O)C=1.C([O-])(O)=O.[Na+].[O-][S:51]([O-:54])(=S)=[O:52].[Na+].[Na+]>C(Cl)Cl>[Si:1]([O:18][CH2:19][C:20]1[C:25]([S:51]([CH3:34])(=[O:54])=[O:52])=[CH:24][C:23]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[C:22]([I:33])[CH:21]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1
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참가 물질

6

반응물 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 89814652N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide

생성물 1

HCID 89814617N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylsulfonyl)phenyl)methanesulfonamide수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A suspension of crude N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide and mCPBA (8.9 g, 51.6 mmol) in CH2Cl2 (100 mL) was stirred for 2 h at rt. Sat. aq. NaHCO3 (50 mL) and Na2S2O3 (50 mL) were added and the layers separated. The aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel eluting with EtOAc/hexanes (3/7) to provide N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylsulfonyl)phenyl)methanesulfonamide (8.8 g, 80% yield for two steps). For N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide: LC-MS m/z 612 [M+H]+. For N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylsulfonyl)phenyl)methanesulfonamide: LC-MS m/z 644 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 8.25 (s, 1H), 8.08 (s, 1H), 7.67-7.65 (m, 4H), 7.46-7.37 (m, 6H), 6.77 (s, 1H), 5.05 (s, 2H), 3.11 (s, 3H), 2.83 (s, 3H), 1.12 (s, 9H).

후처리

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×100 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography over silica gel eluting with EtOAc/hexanes (3/7)

출처 및 근거

ORD 기록
ord-073a5f84ee2940e2810f19fee591470c
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09388190B2

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