Hydrochloric Acid → (2S)-2-hydroxy-3,3-dimethyl-4-[(methylsulfonyl)oxy]butyl methanesulfonate

HRID 1182297ノート

反応式

HRID 1182297 の反応式
[CH3:1][C:2]([CH3:9])([CH2:7][OH:8])[C@H:3]([OH:6])[CH2:4][OH:5].[CH3:10][S:11](Cl)(=[O:13])=[O:12].Cl>N1C=CC=CC=1.ClCCl>[CH3:10][S:11]([O:5][CH2:4][C@@H:3]([OH:6])[C:2]([CH3:9])([CH3:1])[CH2:7][O:8][S:11]([CH3:10])(=[O:13])=[O:12])(=[O:13])=[O:12]

参加物

6

反応物 3

HCID 313Hydrochloric Acid2 回HCID 31297Methanesulfonyl chlorideHCID 11020933(S)-3,3-Dimethylbutane-1,2,4-triol

生成物 1

HCID 58981714(2S)-2-hydroxy-3,3-dimethyl-4-[(methylsulfonyl)oxy]butyl methanesulfonate収率 52%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

To a 0° C. solution of 25.3 g (189 mmol) of (2S)-3,3-dimethyl-1,2,4-butanetriol in 170 mL of pyridine was added dropwise 29.1 mL (378 mmol) of methanesulfonyl chloride. The reaction mixture was allowed to warm slowly to room temperature, and was stirred for 18 h. It was then diluted with dichloromethane. To the resulting solution was added 200 mL of 1 N hydrochloric acid, followed by enough concentrated hydrochloric acid to acidify the aqueous phase (pH=2). The mixture was extracted with dichloromethane, and the combined extracts were washed with brine and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with acetone:dichloromethane (1:9) to afford 21.75 g (52%) of (2S)-2-hydroxy-3,3-dimethyl-4-[(methylsulfonyl)oxy]butyl methanesulfonate. 1H-NMR (300 MHz, DMSO-d6): δ 5.48 (d, J=6 Hz, 1H), 4.30 (dd, J=3 Hz, J=10 Hz, 1H), 4.05–3.91 (m, 3H), 3.16 (d, J=4 Hz, 6H), 0.90 (d, J=13 Hz, 6H).

後処理

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe combined extracts were washed with brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with acetone:dichloromethane (1:9)

出典と根拠

ORDレコード
ord-534ce4812af5490c906adef3d751526a
出典データセット
uspto-grants-2007_10
特許番号
US07288541B2

反応ノート

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