1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67076893, compound

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Reaction Steps

5.22 g (16.0 mmol) 3-(2-Amino-phenoxy)-2-tert-butoxycarbonylamino-pentanoic acid and 3.12 g (15.9 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochloride in 71 ml dimethylformamide were stirred overnight at room temperature. Extraction with saturated aqueous sodium hydrogencarbonate/ethylacetate and chromatography on silicagel with ethylacetate/heptane 1:2 followed by chromatography on Chiralpak AD with heptane/ethanol 80:20 yielded 0.46 g (−)-((6R,7S)-6-ethyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester, [1H-NMR (ppm, CDCl3): 1.11(t, 3H), 1.42 (s, 9H), 1.5–1.9 (m, 2H), 4.53–4.62 (m, 1H), 4.76 (mc, 1H), 5.57 (d, 1H), 6.94–6.97 (m, 1H), 7.0–7.1 (m, 1H), 7.1–7.18 (m, 2H), 8.08 (broad, 1H)], and 590 mg (+)-((6S,7R)-6-ethyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester, [1H-NMR (ppm, CDCl3): 1.11(t, 3H), 1.42 (s, 9H), 1.5–1.9 (m, 2H), 4.53–4.62 (m, 1H), 4.76 (mc, 1H), 5.57 (d, 1H), 6.94–6.97 (m, 1H), 7.0–7.1 (m, 1H), 7.1–7.18 (m, 2H), 7.39 (broad, 1H)].

Provenance & Evidence