Methanol → 2-(N-Methylbenzylamino)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic Acid Tert-Butyl Ester

HRID 18729

Reaktionsgleichung

[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9](SC)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CO>ClCCl>[C:21]([O:20][C:18]([N:10]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:9]1[N:28]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:27])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

A mixture of intermediate 59 (0.4 g, 0.00109 mol), N-methylbenzylamine (0.42 mL, 0.00326 mol) and MeOH (0.1 mL) is heated at 95° C. for 2 days. The reaction mixture is cooled to RT, dichloromethane is added and the mixture is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (80:20-75:25) gives 110 mg of the product 81. 1H NMR (CDCl3) δ 7.50-7.20 (m, 6 H), 7.10-6.90 (m, 7 H), 6.90-6.75 (m, 2 H), 5.52 (q, 2 H), 4.84 (d, 1 H), 4.52 (d, 1 H), 2.97 (s, 3 H), 1.45 (s, 9 H); MS: m/z 442 (M++1).

Aufarbeitung

temperatureThe reaction mixture is cooled to RT
customthe mixture is purified by chromatography on silica gel
washgradient elution with heptane:EtOAc (80:20-75:25)

Quellen und Nachweise

ORD-Eintrag: ord-be470216a5eb4e859a546c575261ba46
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07741493B2

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