Triethylamine → Methanesulfonic acid 2-(2-oxo-2,3-dihydro-benzooxazol-5-yl)-ethyl ester

HRID 456597Notes

Reaction equation

HRID 456597 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15](=[O:17])[NH:14][C:13]=2[CH:18]=1.C(N(CC)CC)C>O1CCCC1>[O:17]=[C:15]1[NH:14][C:13]2[CH:18]=[C:9]([CH2:8][CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:10]=[CH:11][C:12]=2[O:16]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 179812295-(2-Hydroxy-ethyl)-3H-benzoxazol-2-one

Product 1

HCID 86760443Methanesulfonic acid 2-(2-oxo-2,3-dihydro-benzooxazol-5-yl)-ethyl esterYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (0.23 ml, 2.93 mmol) was added dropwise, at room temperature, to a solution of alcohol (b) (0.5 g, 2.79 mmol) and triethylamine (0.41 ml, 3 mmol) in tetrahydrofuran (20 ml) and the mixture was stirred for 3 hours. More methane sulfonyl chloride (0.1 ml) and triethylamine (0.1 ml) were added and stirring was continued over night. The same amount of reagent was added yet again and stirring continued for 2 hours. The solvent was then concentrated, the residue was suspended in water and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated. The solid residue was chromatographed on silica gel eluting with heptane-ethyl acetate (1-1) to give the product (0.2 g, 28%).

Workup

  1. stirringstirring
  2. waitwas continued over night
  3. additionThe same amount of reagent was added yet again
  4. stirringstirring
  5. waitcontinued for 2 hours
  6. concentrationThe solvent was then concentrated
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe solid residue was chromatographed on silica gel eluting with heptane-ethyl acetate (1-1)

Sources & evidence

ORD record
ord-771d18febf8d47fd9363ab5311ab34fe
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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