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

HRID 750392ノート

反応式

HRID 750392 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 52.1%

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-1,2,4butanetriol in 170 mL of pyridine was added dropwise 29.1 mL (378 mmol) of methanesulfonyl chloride. The reaction mixture was allowed to slowly warm to room temperature, stirred for 18 h, and then diluted with dichloromethane. To the mixture was added 200 mL of 1N hydrochloric acid followed by concentrated hydrochloric acid until the pH of the aqueous phase was brought to a value of 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 10% acetone in dichloromethane to afford 21.75 g (52.10%) 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=2 Hz, J=10 Hz, 1H), 3.91-4.05 (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 10% acetone in dichloromethane

出典と根拠

ORDレコード
ord-e7197860bd3641209b629162d931ce30
出典データセット
uspto-grants-2008_07
特許番号
US07402606B2

反応ノート

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