Cesium carbonate → HCID 86612854, compound

Reaction equation

[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][NH:5][C:6](=[O:8])[CH3:7].[O:13]1[CH2:15][C@H:14]1[CH2:16]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>>[O:13]1[CH2:15][C@H:14]1[CH2:16][O:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][NH:5][C:6](=[O:8])[CH3:7]

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

HCID 12714526N-[(2-Hydroxyphenyl)methyl]acetamide

Product 1

HCID 86612854HCID 86612854, compoundYield 65.2%

Procedure

A mixture of N-(2-hydroxybenzyl)acetamide (382 mg, 2.31 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (599 mg, 2.31 mmol) and Cs2CO3 (901 mg, 2.77 mmol) in DMP (5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-80% ethyl acetate in petroleum spirit) to give the subtitled compound (333 mg).