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Ethyl Acetate → Methanesulfonic acid (4S,5S)-5-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-YL)-methanesulfonyloxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

HRID 1268708
ノート
印刷プレビュー

反応式

HRID 1268708 の反応式
[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@@H:7]([C@@H:9]2[C@H:13]([CH2:14][OH:15])[O:12][C:11]([CH3:17])([CH3:16])[O:10]2)[OH:8])[CH2:4][O:3]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]([O:8][S:20]([CH3:19])(=[O:22])=[O:21])[C@@H:9]2[C@H:13]([CH2:14][O:15][S:20]([CH3:19])(=[O:22])=[O:21])[O:12][C:11]([CH3:17])([CH3:16])[O:10]2)[CH2:4][O:3]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 13963403HCID 13963403、化合物

生成物 1

HCID 11026162Methanesulfonic acid (4S,5S)-5-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-YL)-methanesulfonyloxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester収率 98%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

4.1 g (0.016 mol) of {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4R,5S)-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)-methanol from the aforementioned Experimental Example 2 were dissolved in a mixed solvent of 1.0 L dichloromethane and 25 mL pyridine. After cooling the mixture to 0° C., 18 mL (0.236 mol) of methanesulfonyl chloride were added and the resulting solution was stirred for 5 h at 0° C. Saturated sodium bicarbonate solution was added and the compound was extracted with chloroform. The extract was dried, filtered, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography using the eluant hexane:ethyl acetate=2:1 to obtain 6.4 g (yield: 98%) of methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester as an oil.

後処理

  1. extractionthe compound was extracted with chloroform
  2. customThe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-68f747b8e65f449a8471b0a58b2e9cfe
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07199127B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート