Carboxylic Derivatives
a technology of carboxylic derivatives and derivatives, applied in the field of carboxylic derivatives, can solve the problems of not being universally accepted as a diagnosis and the risk of cardiovascular morbidity and mortality is greatly increased for individuals with insulin resistan
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example 1
(2S)-3-(4-{2-[(2,4-Difluorobenzyl)(octyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic acid
(i) N-(2,4-Difluorobenzyl)octanamide
[0399] To a solution of 2,4-difluorobenzylamine (0.43 g, 3.0 mmol) in methylene chloride (30 mL) were added octanoic acid (0.43 g, 3.0 mmol) and DMAP (0.37 g, 3.0 mmol) followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.60 g, 3.1 mmol) and the reaction mixture was stirred at room temperature overnight. The resulting solution was diluted with methylene chloride (100 mL) and the organic phase washed with 5% HCl (3×75 mL), aqueous NaHCO3 (75 mL), and brine (75 mL) and dried over anhydrous Na2SO4. Concentration in vacuo afforded 0.78 g (96%) of an oil, which solidified upon standing.
[0400]1H NMR (500 MHz, CDCl3): δ 0.81-0.90 (m, 3H), 1.18-1.33 (m, 8H), 1.54-1.66 (m, 2H), 2.12-2.21 (m, 2H), 4.42 (d, 2H), 5.82 (bs, 1H), 6.73-6.87 (m, 2H), 7.32 (m, 1H).
(ii) N-(2,4-Difluorobenzyl)-N-octylamine hydrochloride
[0401] N-(2,4-Difluorobenzyl)oct...
example 2
(2S)-3-(4-{2-[(2,4-Difluorobenzyl)(nonyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic acid
(i) N-(2,4-Difluorobenzyl)nonanamide
[0407] To a solution of 2,4-difluorobenzylamine (0.47 g, 3.3 mmol) in methylene chloride (30 mL) were added nonanoic acid (0.52 g, 3.3 mmol) and DMAP (0.40 g, 3.3 mmol) followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.67 g, 3.5 mmol) and the reaction mixture was stirred at room temperature overnight. The resulting solution was diluted with methylene chloride (100 mL) and the organic phase washed with 5% HCl (3×75 mL), aqueous NaHCO3 (75 mL), and brine (75 mL) and dried over anhydrous Na2SO4. Concentration in vacuo afforded 0.87 g (93%) of an oil, which solidified upon standing.
[0408]1H NMR (600 MHz, CDCl3): δ0.80-0.86 (m, 3H), 1.16-1.28 (m, 10H), 1.53-1.62 (m, 2H), 2.11-2.17 (m, 2H), 4.37 (d, 2H), 6.12 (bs, 1H), 6.70-6.81 (m, 2H), 7.27 (m, 1H).
(ii) (N-(2,4-Difluorobenzyl)-N-nonylamine hydrochloride
[0409] N-(2,4-Difluorobenzyl)no...
example 3
(2S)-3-(4-{2-[(2,4-Difluorobenzyl)(4-ethylbenzyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic acid
(i) N-(2,4-Difluorobenzyl)-4-ethylbenzamide
[0415] To a solution of 2,4-difluorobenzylamine (3.58 g, 25.0 mmol) in methylene chloride (250 mL) were added 4-ethylbenzoic acid (3.94 g, 26.3 mmol) and DMAP (3.36 g, 27.5 mmol) followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.27 g, 27.5 mmol) and the reaction mixture was stirred at room temperature overnight. The resulting solution washed with 5% HCl (3×100 mL), saturated aqueous NaHCO3 (100 mL), and brine (100 mL) and dried over Na2SO4. Concentration in vacuo afforded 6.49 g (94%) of white solid.
[0416]1H NMR (400 MHz, CDCl3): δ 1.24 (t, 3H), 2.69 (q, 2H), 4.64 (d, 2H), 6.45 (bs, 1H), 6.77-6.90 (m, 2H), 7.25 (d, 2H), 7.41 (m, 1H), 7.69 (d, 2H).
(ii) N-(2,4-Difluorobenzyl)-N-(4-ethylbenzyl)amine
[0417] N-(2,4-Difluorobenzyl)-4-ethylbenzamide (6.20 g, 22.5 mmol) was dissolved in freshly distilled THF (220 mL) and co...
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