4-Toluenesulfonyl chloride → HCID 59226402, 화합물

HRID 1920230노트

반응식

HRID 1920230 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 59226402HCID 59226402, 화합물수율 68%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3d3cbe2ad73d4fc3aee665c0321623a8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168794B2

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