1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 16122905, compound

Participants

Reaction Steps

A mixture of 5.6 g of N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine, 5.0 g of (−)-(2R)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid, 0.8 g of 1-hydroxybenzotriazole hydrate and 5 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 3 mL of triethylamine in 100 mL in dichloromethane was stirred overnight. The mixture was concentrated under reduced pressure and partitioned between 100 mL of ethyl acetate and 100 mL of saturated sodium carbonate, dried over magnesium sulfate and concentrated under reduced pressure. Flash chromatography (20%-50% ethyl acetate/hexanes gradient elution) gave the product as a resin: MS (m+1)=449.3; H NMR (400 MHz, CDCl3) 7.3-6.7 (complex m, 5H), 4.6 (br d, 1H), 6.8-6.7 (m, 2H), 4.4 (d, 1H), 4.2 (m, 4H), 4.15 (q, 1H), 4.08 (br d, 1H), 3.95 (m, 1H), 3.5 (m, 1H), 3.2 (m, 1H), 3.0 (dd, 1H), 2.2 (m, 1H), 2.0 (m, 1H) 1.45 (2×s, 9H), 0.9 (dd, 6H).

Provenance & Evidence