N,N-Dimethylglycine → HCID 178462420, compound

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Reaction Steps

A solution of (1R,2R)-2-[[trans-2-[(1E,3E)-4-(4-cyano-2-fluorophenyl)-1,3-butadienyl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propyl 2-(hydroxymethyl)benzoate (640.7 mg, 0.95 mmol) obtained from Example 17-(4) in dichloromethane (20 ml) was cooled to 0° C., and then 4-(N,N-dimethylamino)pyridine (254.5 mg, 2.1 mmol), N,N-dimethylglycine (117.2 mg, 1.14 mmol), and 2-chloro-1,3-dimethylimidazolinium chloride (256.1 mg, 1.52 mmol) were added thereto. The reaction mixture was stirred at room temperature for 3 hours, diluted with ethyl acetate, and then the organic layer was washed successively with a saturated aqueous solution of ammonium chloride and with a saturated aqueous solution of sodium chloride. The solvent was evaporated under reduced pressure, and then the residue was subjected to chromatography on a silica gel (40 g) column (eluent; ethyl acetate:methanol=100:3) to give a mixture of the title compound and 1,3-dimethyl-2-imidazolidinone. The mixture was purified by recycle preparative HPLC [LC-908; Japan Analytical Industry Co., Ltd.; GPC column JAIGEL-1H (20 mm i.d. ×600 mm) and JAIGEL-2H (20 mm i.d. ×600 mm) connected in series for use; solvent, chloroform] to afford the title target compound (368.1 mg, 51% yield) as a colorless amorphous solid.

Provenance & Evidence