4-Toluenesulfonyl chloride → ((5R)-2-oxo-1,3-oxazolidin-5-yl)methyl4-methylbenzenesulfonate

HRID 650969Notes

Reaction equation

HRID 650969 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[Cl-].[Na+].O.O>N1C=CC=CC=1>[O:8]=[C:6]1[NH:5][CH2:4][C@H:3]([CH2:2][O:1][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[O:7]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 10236003(5R)-5-(hydroxymethyl)-1,3-oxazolidin-2-oneHCID 23713072Sodium chloride dihydrate

Product 1

HCID 2793763((5R)-2-oxo-1,3-oxazolidin-5-yl)methyl4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (5R)-5-(hydroxymethyl)-1,3-oxazolidin-2-one (10.0 g), prepared as described in Tetrahedron: Asymmetry 1995, 6, 1181-1190, in pyridine (60 mL) at −10° C. was treated with para-toluenesulfonyl chloride (21.2 g), stirred for 2 hours, poured into 1:1 brine/water (100 mL), and extracted with ethyl acetate. The extract was washed with 1:1 saturated sodium bicarbonate/water and 1:1 brine/water, and the washes were back extracted with ethyl acetate. The combined extracts was dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 272 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 7.80 (d, 2H), 7.39 (d, 2H), 4.80 (m, 1H), 4.18 (d, 2H), 3.70 (t, 1H), 3.50 (dd, 1H), 2.45 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 1:1 saturated sodium bicarbonate/water and 1:1 brine/water
  3. extractionthe washes were back extracted with ethyl acetate
  4. dry with materialThe combined extracts was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5c581483aa0943ae8a4be73ea380bc95
Source dataset
uspto-grants-2001_08
Patent number
US06277868B1

Reaction notes

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