Benzyl isocyanate → Methyl 5-oxo-1-(3-{(benzylamino)carbonyl amino}phenyl)pyrrolidine-3-carboxylate

HRID 22902

Reaktionsgleichung

Reaktionsgleichung von HRID 22902
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([N:18]2[C:22](=[O:23])[CH2:21][CH:20]([C:24]([O:26][CH3:27])=[O:25])[CH2:19]2)[CH:15]=[CH:16][CH:17]=1>ClCCl>[O:23]=[C:22]1[N:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][C:9]([NH:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH:13]=2)[CH2:19][CH:20]([C:24]([O:26][CH3:27])=[O:25])[CH2:21]1

Komponenten

4

Edukt 2

HCID 76639Benzyl isocyanateHCID 22591876Methyl 1-(3-aminophenyl)-5-oxopyrrolidine-3-carboxylate

Produkt 1

HCID 22591825Methyl 5-oxo-1-(3-{(benzylamino)carbonyl amino}phenyl)pyrrolidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Benzyl isocyanate (2.3 mL, 18.6 mmol, 1.2 equiv) was added to a solution of methyl 1-(3-aminophenyl)-5-oxopyrrolidine-3-carboxylate (3.6169 g, 15.4 mmol, 1 equiv) in dichloromethane (77 mL). The resulting solution was stirred at 23° C. for 27 hr, during which time a white precipitate formed. The reaction was filtered, and the solid was collected to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.68 (s, 1H), 7.76 (t, 1H, J=1.8 Hz), 7.13-7.36 (m, 8H), 6.59 (t, 1H, J=5.9 Hz), 4.30 (d, 2H, J=5.9 Hz), 4.03 (dd, 1H, J=9.7 Hz, 8.7 Hz), 3.94 (dd, 1H, J=9.5 Hz, 6.1 Hz), 3.68 (s, 3H), 3.41-3.50 (m, 1H), 2.80 (dd, 1H, J=17.0 Hz, 9.5 Hz), 2.71 (dd, 1H, J=17.0 Hz, 7.0 Hz). MS: (+) 368.0 (M+H), 385.5, 390.0, 735.5; (−) 366.0 (M−H), 426.0, 733.5, 793.5.

Aufarbeitung

  1. customformed
  2. filtrationThe reaction was filtered
  3. customthe solid was collected

Quellen und Nachweise

ORD-Eintrag
ord-8c8d8d76bf8f4994939cf6b564af15fb
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849639B2

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