Triethylamine → HCID 88472595, compound

Participants

Reaction Conditions

Reaction Steps

To a magnetically stirred solution of the benzoic acid (prepared as in Example 1 Part C) (1.97 g, 7.57 mM) in dry acetone (20 ml) at -10° C. (dry ice/acetone) and under argon was added isobutylchloroformate (1.1 ml, 8.48 mM) followed by Et3N (1.2 ml, 7.57 mM). This was stirred for 30 minutes at -10° C., then filtered into a cooled solution (-15° C.) of the hydrolysis product prepared as described in Example 4 Part D(1). The resulting mixture was stirred for 30 minutes at -10° C. (dry ice/acetone) then allowed to warm to room temperature and stirred overnight. The reaction mixture was then partitioned between EtOAc and 5% KHSO4. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to a yellow oil (5.0 g). A flash chromatography on LPS-1 silica gel eluting with (7:1) CH2Cl2 -acetone yielded 680 mg (20%) of the title amide as a white solid with consistent NMR spectral data.

Provenance & Evidence