4-Toluenesulfonyl chloride → HCID 59226402、化合物

HRID 73592ノート

反応式

HRID 73592 の反応式
[OH:1][CH2:2][C@@H:3]1[CH:7]([CH:8]([CH3:11])[CH2:9][OH:10])[O:6][C:5](=[O:12])[NH:4]1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.CCO[C:27]([CH3:29])=O>N1C=CC=CC=1>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:10][CH2:9][CH:8]([CH:7]2[O:6][C:5](=[O:12])[NH:4][C@@H:3]2[CH2:2][O:1][S:19]([C:27]2[CH:29]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH3:11])(=[O:21])=[O:20])=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 59226593(4R)-4-(hydroxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one

生成物 1

HCID 59226402HCID 59226402、化合物収率 68%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of (4R)-4-(hydroxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one (1.0 equiv.) in pyridine (0.15 M) at 0° C. was added p-toluenesulfonylchloride (2.1 equiv.). The solution was allowed to warm to rt as it stirred for 14 hours, at which time EtOAc was added and the solution was washed with H2O (3×), CuSO4(sat.) (2×), H2O, Na2CO3(sat.) and NaCl(sat.), dried over MgSO4, filtered, concentrated and purified by silica gel chromatography (75% EtOAc/hexanes eluant) yielding 2-((4R)-2-oxo-4-(tosyloxymethyl)oxazolidin-5-yl)propyl 4-methylbenzenesulfonate (68%). LCMS (m/z): 484.1 (MH+); LC Rt=4.06 min.

後処理

  1. additionwas added
  2. washthe solution was washed with H2O (3×), CuSO4(sat.) (2×), H2O, Na2CO3(sat.) and NaCl(sat.)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (75% EtOAc/hexanes eluant)

出典と根拠

ORDレコード
ord-2155906fac214e1ea30417c84f971051
出典データセット
uspto-grants-2014_09
特許番号
US08829193B2

反応ノート

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