Dimethylformamide → ({[5-(2-Azidoethyl)-2,3-dichlorophenyl]methyl}oxy)(1,1-dimethylethyl)dimethylsilane

HRID 337590노트

반응식

HRID 337590 반응식
CN(C=O)C.CS(O[CH2:11][CH2:12][C:13]1[CH:18]=[C:17]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:16]([Cl:28])=[C:15]([Cl:29])[CH:14]=1)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+]>CCOCC>[N:30]([CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([Cl:29])[C:16]([Cl:28])=[C:17]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:18]=1)=[N+:31]=[N-:32]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 866516682-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl methanesulfonate

생성물 1

HCID 86651669({[5-(2-Azidoethyl)-2,3-dichlorophenyl]methyl}oxy)(1,1-dimethylethyl)dimethylsilane

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a DMF (0.4 M) solution of 2-[3,4-dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl methanesulfonate (1 eq.) from Step 5, Amine 26 was added at RT sodium azide (5 eq.). The resulting solution was stirred at RT for 12 h and then at 80° C. for 3 h. The reaction mixture was then diluted with ether and washed with water. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a pink oil.

후처리

  1. waitat 80° C. for 3 h
  2. washwashed with water
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo

출처 및 근거

ORD 기록
ord-5a8506b38f1142b391b14139d03e4133
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889714B2

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