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

HRID 2407866ノート

反応式

HRID 2407866 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3b0dcb9a884d4a40b4f722d83648ff2d
出典データセット
uspto-grants-2014_08
特許番号
US08808703B2

反応ノート

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