4-Toluenesulfonyl chloride → HCID 59201488、化合物

HRID 451877ノート

反応式

HRID 451877 の反応式
[CH:1]1([O:7][C:8](=[O:29])[CH2:9][CH2:10][C@@H:11]([CH2:27][OH:28])[CH2:12][C@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[N:14]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[S:30](Cl)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH:1]1([O:7][C:8](=[O:29])[CH2:9][CH2:10][C@@H:11]([CH2:27][O:28][S:30]([C:33]2[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH2:12][C@H:13]2[CH2:17][O:16][C:15]([CH3:18])([CH3:19])[N:14]2[C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

5

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 59201656HCID 59201656、化合物

生成物 1

HCID 59201488HCID 59201488、化合物収率 98%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

The (S)-tert-butyl 4-((R)-5-(cyclohexyloxy)-2-(hydroxymethyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate (4.97 g, 12.0 mmol, 1.0 equiv), DMAP (1.47 mg, 12.0 mmol, 1.0 equiv) and tosyl chloride (9.2 g, 48.2 mmol, 4.0 equiv) were dissolved in pyridine (100 mL) and the solution stirred for 18 hr. The pyridine was removed in vacuo and the residue taken up in EtOAc/0.5 M HCl. The layers were separated, and the organic layer washed with 10% K2CO3, brine, dried over Na2SO4, filtered and evaporated. The tosylate was purified by flash chromatography on silica, (12 g), eluting with 0-29% EtOAc in hexanes. This afforded 6.66 g (98% yield) of (S)-tert-butyl 4-((R)-5-(cyclohexyloxy)-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate as a white solid. MS ESI +ve m/z 590 (M+Na).

後処理

  1. customThe pyridine was removed in vacuo
  2. customThe layers were separated
  3. washthe organic layer washed with 10% K2CO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe tosylate was purified by flash chromatography on silica, (12 g)
  8. washeluting with 0-29% EtOAc in hexanes

出典と根拠

ORDレコード
ord-994473be16c544929eeb5664b8a77695
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

読み込み中…