Benzyl 3-(2-ethoxy-2-oxoethyl)-3-(3-(4-octylphenyl)ureido)pyrrolidine-1-carboxylate → Ethyl 2-(3-(3-(4-octylphenyl)ureido)pyrrolidin-3-yl)acetate

HRID 1192902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192902
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][C:6]1([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:27][CH:26]=2)=[O:23])[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7]1)[CH3:2]>CCO.[Pd]>[CH2:31]([C:28]1[CH:27]=[CH:26][C:25]([NH:24][C:22](=[O:23])[NH:21][C:6]2([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:39])[CH2:10][CH2:9][NH:8][CH2:7]2)=[CH:30][CH:29]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Komponenten

4

Edukt 1

HCID 66865221Benzyl 3-(2-ethoxy-2-oxoethyl)-3-(3-(4-octylphenyl)ureido)pyrrolidine-1-carboxylate

Produkt 1

HCID 66865457Ethyl 2-(3-(3-(4-octylphenyl)ureido)pyrrolidin-3-yl)acetateAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of benzyl 3-(2-ethoxy-2-oxoethyl)-3-(3-(4-octylphenyl)ureido)pyrrolidine-1-carboxylate (140 mg, 0.26 mmol) in EtOH (5 mL) was purged with nitrogen and Pd/C (25 mg) was added and the flask was purged with hydrogen and stirred for 24 h. The mixture was filtered through celite and concentrated. The residue was dissolved into H2O and lyophilized to give the title compound as a white solid (84 mg, 80%). 1H NMR (400 MHz, CD3OD) δ 7.25 (d, 2H, J=7.9 Hz), 7.08 (d, 2H, J=8.1 Hz), 4.16 (q, 2H, J=7.1 Hz), 4.05-4.02 (m, 1H), 3.51-3.47 (m, 2H), 3.23-3.19 (m, 1H), 2.91-2.87 (m, 1H), 2.57-2.50 (m, 3H), 2.26-2.20 (m, 1H), 1.60-1.57 (m, 2H), 1.31-1.23 (m, 15H), 0.90 (t, 3H, J=6.6 Hz).

Aufarbeitung

  1. additionwas added
  2. customthe flask was purged with hydrogen
  3. filtrationThe mixture was filtered through celite
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved into H2O

Quellen und Nachweise

ORD-Eintrag
ord-9762afc814284022be16a9bcee61835d
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680282B2

Notizen zur Reaktion

Wird geladen…