Dimethylamine → Benzyl [2-(dimethylcarbamoyl)ethyl]carbamate

HRID 1951171

Reaktionsgleichung

[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:2][CH2:3][C:4](O)=[O:5].C[CH2:18][N:19]=[C:20]=NCCCN(C)C.Cl.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.CNC>O1CCOCC1>[CH2:10]([O:9][C:7](=[O:8])[NH:1][CH2:2][CH2:3][C:4](=[O:5])[N:19]([CH3:20])[CH3:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a stirred, cooled (0° C.) solution of Z-Beta-Ala-OH (1.784 g, 8.0 mmol) in dioxane (20 ml) is added EDCI.HCl (2.145 g, 11.2 mmol), hydroxybenzotriazole (1.08 g, 8.0 mmol) and triethylamine (1.56 ml, 11.2 mmol). After stirring at 0° C. for 30 minutes, dimethylamine (0.397 g, 8.8 mmol) is added and stirring continued for a further hour. The reaction mixture was allowed to warm to room temperature and the solvent is removed in vacuo. Initial purification of the crude residue is carried out by flash chromatography of silica eluting with ethyl acetate. The combined organic factions are washed with water (3×20 ml), brine (1×50 ml) and dried over MgSO4. The solvent is removed in vacuo to yield the titled compound as a pale yellow solid.

Aufarbeitung

stirringstirring
waitcontinued for a further hour
temperatureto warm to room temperature
customthe solvent is removed in vacuo
customInitial purification of the crude residue
washThe combined organic factions are washed with water (3×20 ml), brine (1×50 ml)
dry with materialdried over MgSO4
customThe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-4e132a516f2d4c90b2339b822fb1e7d8
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08404684B2

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