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Phosphate → N2-[(3-Iodophenyl)sulfonyl]-N2-{[2-(trimethylsilyl)ethoxy]methyl}glycinamide

HRID 2118312
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HRID 2118312 반응식
[I:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH2:12][C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl.P([O-])([O-])([O-])=O>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]([CH2:23][O:22][CH2:21][CH2:20][Si:19]([CH3:26])([CH3:25])[CH3:18])[CH2:12][C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21895595N2-[(3-Iodophenyl)sulfonyl]glycinamide

생성물 1

HCID 69197160N2-[(3-Iodophenyl)sulfonyl]-N2-{[2-(trimethylsilyl)ethoxy]methyl}glycinamide

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

N2-[(3-Iodophenyl)sulfonyl]glycinamide (0.14 g) was stirred with sodium hydride (60% oil dispersion, 0.02 g) in DMF (2 ml) at 21° under nitrogen for 15 min. 2-Trimethylsilylethoxymethyl chloride (0.08 ml) was added and stirring was continued for 1.5 h. The mixture was poured into pH 6.4 phosphate buffer and the product was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), concentrated and applied to a silica Bond Elut Cartridge (5 g) in dichloromethane containing methanol. The cartridge was eluted with dichloromethane, diethyl ether and ethyl acetate to give the title compound (0.16 g), LCMS RT=3.49 min.

후처리

  1. extractionthe product was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additioncontaining methanol
  6. washThe cartridge was eluted with dichloromethane, diethyl ether and ethyl acetate

출처 및 근거

ORD 기록
ord-9157c2441c4f4a9faa51055c11776a80
출처 데이터셋
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07442837B2

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