Sodium Azide → (R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane

HRID 2407867노트

반응식

HRID 2407867 반응식
CS(O[C@@H:6]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C=O)C>[N:34]([C@H:6]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[N+:35]=[N-:36]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 86678272(S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-yl methanesulfonate

생성물 1

HCID 86678273(R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-yl methanesulfonate (1 eq) and NaN3 (5 eq) in DMF (0.5 M) was stirred at 100° C. over night. The reaction mixture was filtered and washed with DCM. The filtrate was concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-15% EtOAc/Hex to give (R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane as acolorless oil.

후처리

  1. filtrationThe reaction mixture was filtered
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated en vaccuo
  4. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

출처 및 근거

ORD 기록
ord-5f086ede24314a2f9cb2da820c72c744
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08808703B2

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