N-bromobutanimide → (2S)-2-(1-(4-bromophenyl)-3-ethoxy-1,3-dioxopropan-2-yl) 1-tert-butyl pyrrolidine-1,2-dicarboxylate

HRID 1396011

Reaktionsgleichung

Reaktionsgleichung von HRID 1396011
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C1C(=O)N(Br)C(=O)C1.BrC(C(C1C=CC(Br)=CC=1)=O)C(OCC)=O.[C:40]([N:47]1[CH2:54][CH2:53][CH2:52][C@H:48]1[C:49]([OH:51])=[O:50])([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41].CCN(C(C)C)C(C)C>C(Cl)Cl.C(#N)C>[N:47]1([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:54][CH2:53][CH2:52][CH:48]1[C:49]([O:51][C@H:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)=[O:15])=[O:50]

Komponenten

8

Edukt 5

HCID 67184N-bromobutanimideHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 2757149Ethyl 3-(4-bromophenyl)-3-oxopropanoateHCID 13048362Ethyl 2-bromo-3-(4-bromophenyl)-3-oxopropanoate

Produkt 1

HCID 66769804(2S)-2-(1-(4-bromophenyl)-3-ethoxy-1,3-dioxopropan-2-yl) 1-tert-butyl pyrrolidine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The ethyl 3-(4-bromophenyl)-3-oxopropanoate (15 g, 55 mmol) was dissolved in CH2Cl2 (600 mL) and freshly recrystallized NBS (9.8 g, 55 mmol) was added and the solution stirred 18 hr. The reaction mixture was washed with NaHCO3 solution, brine, and dried (MgSO4), filtered, and concentrated to give a residue which was not purified. Ethyl 2-bromo-3-(4-bromophenyl)-3-oxopropanoate (16.5 g, 48 mmol) and N-Boc-L-proline (10 g, 48 mmol) were taken up in acetonitrile (450 mL) and Hunig's base (16 mL, 95 mmol) was added and the solution stirred 18 hr. The solvent was removed by rotorary evaporation and the residue taken up in ethyl acetate, washed with 0.1 N HCl, and brine. 1H NMR (300 MHz, DMSO-d6) δ 7.95 (d, J=8.4 Hz, 2H), 7.79 (d, J=8.4 Hz, 2H), 6.68-6.65 (m, 1H), 4.39-4.30 (m, 1H), 4.21-4.12 (m, 2H), 2.27-2.21 (m, 1H), 2.0-1.95 (m, 1H), 1.90-1.76 (m, 2H), 1.39 (s, 2H), 1.31 (s, 9H), 1.11 (t, J=7.3 Hz, 3H).

Aufarbeitung

  1. washThe reaction mixture was washed with NaHCO3 solution, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas not purified
  7. stirringthe solution stirred 18 hr
  8. customThe solvent was removed by rotorary evaporation
  9. washwashed with 0.1 N HCl, and brine

Quellen und Nachweise

ORD-Eintrag
ord-df1ad2fc25514e7b8340ed5b1d613549
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08900566B2

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