Triethylamine → Methanesulfonic acid 2-(4-methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazol-4-ylmethyl ester

HRID 2233567Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]([CH2:16][O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[C:12]([CH2:14][OH:15])[N:13]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]([CH2:16][O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[C:12]([CH2:14][O:15][S:32]([CH3:31])(=[O:34])=[O:33])[N:13]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.44 g [2-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazol-4-yl]-methanol were dissolved in 30 ml dichloromethane and cooled in an ice bath. 0.29 ml triethylamine were added, followed by the addition of 0.13 ml methanesulfonylchloride. The reaction mixture was stirred at 0° C. for one hour then the ice bath was removed and the resulting mixture stirred at room temperature for an additional hour. The reaction mixture was then washed with water and brine, dried over MgSO4 and the solvent removed in vacuo to obtain 0.55 mg of methanesulfonic acid 2-(4-methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazol-4-ylmethyl ester as an oil which was used without further purification.

Workup

temperaturecooled in an ice bath
customthe ice bath was removed
stirringthe resulting mixture stirred at room temperature for an additional hour
washThe reaction mixture was then washed with water and brine
dry with materialdried over MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-6fbde4e579b94346ba81e80fe07710e2
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709509B2

Reaction notes

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