Dichloromethane → 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl chloride

HRID 74823

Reaktionsgleichung

Reaktionsgleichung von HRID 74823
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O.[Cl:16]CCl>C(Cl)(=O)C(Cl)=O.CN(C=O)C>[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([Cl:16])=[O:15]

Komponenten

5

Edukt 2

HCID 6344DichloromethaneHCID 5736836-Maleimidohexanoic acid

Produkt 1

HCID 114247166-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl chlorideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 65578Oxalyl chlorideLösungsmittel

Versuchsvorschrift

To a stirring solution of 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid (3.15 g, 14.9 mM) in 15 mL of dichloromethane, oxalyl chloride (1.61 mL, 17.9 mM) was added followed by one drop of DMF. The reaction was allowed to stir at room temperature for three hours. The reaction was concentrated in vacuo. The residue was dissolved in a one to one solution of heptane and dichloromethane and then concentrated in vacuo. This process was repeated two more times producing a solid #248 (3.43 g, 100%). 1H NMR (400 MHz, DMSO-d6): δ [7.02 (s, 2H), 3.43 (m, 2H), 2.53 (m, 1H), CH2.18 (m, 1H), 1.54 (m, 4H), 1.26 (m, 2H).]

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionThe residue was dissolved in a one to one solution of heptane and dichloromethane
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6526d9d97fce432eb40b3e77b6705e27
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828401B2

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