Diisopropylethylamine → HCID 102326821, compound

Participants

Reaction Steps

SMTP-0 (50 mg, 78 μmol) was dissolved in acetonitrile (2 mL), and N,N-diisopropylethylamine (50 μl) and trimethylsilyldiazomethane (2.0 M, hexane solution) (150 μl) were added thereto. The mixture was stirred for 24 hours at room temperature. The reaction liquid was concentrated to obtain methyl ether of SMTP-0 (SMTP-0-OMe) (44 mg). SMTP-0-OMe (20 mg, 50 μmol) was dissolved in N,N-dimethylformamide (1 mL), and R-(−)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (25 mg), triethylamine (30 μl) and 4-dimethylaminopyridine (2 mg) were added thereto. The mixture was stirred for 24 hours at room temperature. Water (10 mL) was added to the reaction liquid, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with 1 N HCl, a saturated aqueous solution of sodium hydrogen carbonate and saturated brine, then dried using anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by thin layer chromatography (hexane-ethyl acetate), to obtain SMTP-0-OMe ester of S-α-methoxy-α-(trifluoromethyl)phenylacetylacetic acid (S-MTPA-SMTP-0-OMe) (18 mg).

Provenance & Evidence