N-bromobutanimide → HCID 11615879, Verbindung

HRID 133735

Reaktionsgleichung

Reaktionsgleichung von HRID 133735
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10](=[CH2:21])[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[C:18]([OH:20])=[O:19])=[O:12]>CN(C=O)C>[Br:8][CH2:21][C@:10]1([CH3:9])[O:19][C:18](=[O:20])[C@H:14]2[CH2:15][CH2:16][CH2:17][N:13]2[C:11]1=[O:12]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 11615290(2R)-1-Methacryloylpyrrolidin-2-carboxylic Acid

Produkt 1

HCID 11615879HCID 11615879, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

NBS (16 g, 89.9 mmol) was dissolved in DMF (50 ml) and added at room temperature to a solution of (2R)-1-(2-methylacryloyl)pyrrolidine-2-carboxylic acid (11.5 g, contains 8.0 g of the corresponding starting material, 43.4 mmol) in DMF (50 ml). The mixture was stirred for 20 h and evaporated at 80-90° C. The residue was mixed with water (250 ml) and extracted with ethyl acetate (4×80 ml). The combined ethyl acetate phases were washed with 1 M NaHCO3 solution (2×50 ml) and water (1×50 ml). The organic phase was dried over Na2SO4 and evaporated. The yield of the crude oil was 9.3 g. Ethyl acetate (10 ml) was added and the mixture was stirred in an ice bath. The precipitated product was filtered and washed with cooled ethyl acetate. The yield was 1.2 g. 1H NMR (DMSO-d6): 1.58 (3H, s), 1.75-2.10 (3H, m), 2.25 (1H, m), 3.30-3.55 (2H, m), 3.87 (1H, d, J=11.4 Hz), 4.03 (1H, d, J=11.4 Hz), 4.70 (1H, m).

Aufarbeitung

  1. customevaporated at 80-90° C
  2. additionThe residue was mixed with water (250 ml)
  3. extractionextracted with ethyl acetate (4×80 ml)
  4. washThe combined ethyl acetate phases were washed with 1 M NaHCO3 solution (2×50 ml) and water (1×50 ml)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated
  7. additionEthyl acetate (10 ml) was added
  8. stirringthe mixture was stirred in an ice bath
  9. filtrationThe precipitated product was filtered
  10. washwashed with cooled ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a3a42a8401b34b999aa18c3e4a81b737
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390923B2

Verknüpfte Notizen

Wird geladen…