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

HRID 1348646Notes

Reaction equation

HRID 1348646 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH:5]([CH2:18][CH3:19])[CH:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7](O)=[O:8].Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:14]([O:13][C:11](=[O:12])[NH:10][C@@H:6]1[C:7](=[O:8])[NH:1][C:2]2[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=2[O:4][C@@H:5]1[CH2:18][CH3:19])([CH3:17])([CH3:16])[CH3:15].[C:14]([O:13][C:11](=[O:12])[NH:10][C@H:6]1[C:7](=[O:8])[NH:1][C:2]2[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=2[O:4][C@H:5]1[CH2:18][CH3:19])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21091421HCID 21091421, compound

Product 2

HCID 67076893HCID 67076893, compoundHCID 67076914HCID 67076914, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)].

Workup

  1. extractionExtraction with saturated aqueous sodium hydrogencarbonate/ethylacetate and chromatography on silicagel with ethylacetate/heptane 1:2

Sources & evidence

ORD record
ord-470045440f004411be5d01a994cf7871
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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