Tetrabutylammonium Fluoride → (S)-2-azido-3-(hexadecyloxy)propan-1-ol

HRID 2204972노트

반응식

HRID 2204972 반응식
[N:1]([C@H:4]([CH2:14][O:15][CH2:16][CH2:17][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][CH3:31])[CH2:5][O:6][Si](C(C)(C)C)(C)C)=[N+:2]=[N-:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOCC>[N:1]([C@H:4]([CH2:14][O:15][CH2:16][CH2:17][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][CH3:31])[CH2:5][OH:6])=[N+:2]=[N-:3]

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86678273(R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane

생성물 1

HCID 86678274(S)-2-azido-3-(hexadecyloxy)propan-1-ol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of (R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane (1 eq), and 1M TBAF in THF (1.1 eq) in THF (0.2 M) was stirred at 25° C. for 20 minutes. The reaction was diluted with Et2O and washed with saturated NH4Cl, H2O, and brine. The organic phase was dried over anhydrous sodium sulfate and concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-30% EtOAc/Hex to give (S)-2-azido-3-(hexadecyloxy)propan-1-ol as a colorless oil.

후처리

  1. washwashed with saturated NH4Cl, H2O, and brine
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated en vaccuo
  4. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

출처 및 근거

ORD 기록
ord-8fe1607a277e4924a91a905b15d30082
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365506B2

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