Methanesulfonyl chloride → (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-yl methanesulfonate

HRID 2407866노트

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HRID 2407866 반응식
[Si:1]([O:8][CH2:9][C@@H:10]([OH:29])[CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>N1C=CC=CC=1>[CH3:30][S:31]([O:29][C@@H:10]([CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])(=[O:33])=[O:32]

참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 10960980(S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

To a solution of (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol (1 eq) in pyridine (0.5 M) at 0° C., was added MsCl (2 eq). The reaction was stirred at 0° C. for 1 h and quenched by H2O. The aqueous phase was extracted with DCM. The combined organic phases were washed with H2O, and the aqueous phase was back extracted with DCM. The combined organic phases were washed with saturated NaHCO3 and brine, dried over anhydrous Na2SO4 and concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-15% EtOAc/Hex to give (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-yl methanesulfonate as a colorless oil.

후처리

  1. customquenched by H2O
  2. extractionThe aqueous phase was extracted with DCM
  3. washThe combined organic phases were washed with H2O
  4. extractionthe aqueous phase was back extracted with DCM
  5. washThe combined organic phases were washed with saturated NaHCO3 and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated en vaccuo
  8. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

출처 및 근거

ORD 기록
ord-3b0dcb9a884d4a40b4f722d83648ff2d
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08808703B2

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