4-Toluenesulfonyl chloride → HCID 59226402, compound

HRID 1523470Notes

Reaction equation

HRID 1523470 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 59226402HCID 59226402, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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 eluent) 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.

Workup

  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 eluent)

Sources & evidence

ORD record
ord-9910d1a3e6444018ae2a0a7ec0c9bf57
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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