Diethyl acetylenedicarboxylate → 5-Ethoxycarbonylmethyl-3-(2-methoxy-phenyl)-2-methyl-2,5-dihydro-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester

HRID 1822700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1822700
[OH:1][N:2]([CH3:13])[C:3](=[NH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].[C:14]([C:21]([O:23][CH2:24][CH3:25])=[O:22])#[C:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH2:24]([O:23][C:21]([C:14]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:1][N:2]([CH3:13])[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:10][CH3:11])=[N:12]1)=[O:22])[CH3:25]

Komponenten

4

Edukt 2

HCID 69803Diethyl acetylenedicarboxylateHCID 22169629N-Hydroxy-2-methoxy-N-methyl-benzamidine

Produkt 1

HCID 235684175-Ethoxycarbonylmethyl-3-(2-methoxy-phenyl)-2-methyl-2,5-dihydro-[1,2,4]oxadiazole-5-carboxylic acid ethyl esterAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of N-hydroxy-2-methoxy-N-methyl-benzamidine (3.3 g) in ethanol (100%) was added diethyl acetylenedicarboxylate (3.2 mL, 20 mmol) and the resulting mixture stirred for 2 h at room temperature. The reaction mixture was then concentrated and purified on silica gel column using (3:7 to 2:3 ethyl acetate/hexanes) to afford the title product as a yellow oil (4.93 g, 70% yield). 1HNMR (500 MHz, CDCl3) δ: 7.56 (1H, dd, 7.6, 1.5 Hz), 7.44 (1H, td, J=7.6, 1.6 Hz), 6.99 (1H, t, 7.5 Hz), 6.95 (1H, d, J=8.2 Hz), 4.36–4.10 (4H, m), 3.85 (3H, s), 3.43 (1H, d, J=16.48 Hz), 3.05 (3H, s), 3.04 (1H, d, J=16.48 Hz), 1.32 (3H, t, J=7.02 Hz), 1.25 (3H, t, J=7.02 Hz). HRMS (ESI) calcd for C17H23N2O6 (M+H): 351.1556; found: 351.1553.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-5284a8dcb8154bedae1888152c1d4932
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07037908B2

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