Triethylamine → Tert-butyl 3-(2-ethoxy-2-oxoethyl)-3-(5-(phenylethynyl)furan-2-carboxamido)-azetidine-1-carboxylate

HRID 1192913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192913
[NH2:1][C:2]1([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.CCN(CC)CC.[C:26]1([C:32]#[C:33][C:34]2[O:38][C:37]([C:39](ON3C(=O)CCC3=O)=[O:40])=[CH:36][CH:35]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][C:2]1([NH:1][C:39]([C:37]2[O:38][C:34]([C:33]#[C:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:35][CH:36]=2)=[O:40])[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])[CH2:3]1)[CH3:18]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 574408102,5-Dioxopyrrolidin-1-yl 5-(phenylethynyl)furan-2-carboxylateHCID 58109966Tert-butyl 3-amino-3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate

Produkt 1

HCID 66865345Tert-butyl 3-(2-ethoxy-2-oxoethyl)-3-(5-(phenylethynyl)furan-2-carboxamido)-azetidine-1-carboxylateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of tert-butyl 3-amino-3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate (130 mg, 0.503 mmol) in DMF (3 mL) was treated with NEt3 (0.19 mL, 1.37 mmol), and 2,5-dioxopyrrolidin-1-yl 5-(phenylethynyl)furan-2-carboxylate, prepared as described in Preparation 5 (141 mg, 0.457 mmol). The reaction was stirred overnight, at room temperature, then the solvent removed in vacuo and the crude product purified by column chromatography to obtain the title compound (168 mg, 81%). 1H NMR (400 MHz, CDCl3) δ 7.57 (m, 2H), 7.40 (m, 3H), 7.12 (s, 1H), 7.04 (s, 1H), 6.70 (s, 1H), 4.17 (m, 4H), 4.03 (d, 2H, J=9.6 Hz), 3.17 (s, 2H), 1.45 (s, 9H), 1.26 (t, 3H, J=7.2 Hz); MS ESI 453.2 [M+H]+, calcd for [C25H28N2O6+H]+ 453.51.

Aufarbeitung

  1. customprepared
  2. customthe solvent removed in vacuo
  3. customthe crude product purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5e23ef891c124963aa390eb1d192fc06
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680282B2

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