1,2-Dichloroethane → HCID 68921124, Verbindung

HRID 1785986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1785986
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C@@H:15]([CH3:23])[CH2:14]2)[C:9](=[O:12])[CH2:10][OH:11])=[CH:4][CH:3]=1.C(Cl)CCl.[C:28](O)(=[O:30])[CH3:29]>C(Cl)Cl>[C:28]([O:11][CH2:10][C:9]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@H:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C@@H:15]([CH3:23])[CH2:14]1)=[O:12])(=[O:30])[CH3:29]

Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 68918824HCID 68918824, Verbindung

Produkt 1

HCID 68921124HCID 68921124, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(4-Chlorophenyl)-2-hydroxy-N-[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (300 mg, 0.91 mmol, 1 equ.) was dissolved in methylene chloride (3 mL). To this solution was added EDC (464 mg, 2.7 mmol, 3 equ.) and acetic acid (164 mg, 2.7 mmol, 3 equ.) and the reaction mixture was stirred at room temperature for 20 h. Reaction mixture was concentrated and the residue dissolved in ethyl acetate and washed with water, brine, and then dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (methylene chloride/methanol: 99/1 to 98/2 gradient) to afford 2-{(4-chlorophenyl)[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-2-oxoethyl acetate (240 mg, 84%).

Aufarbeitung

  1. customReaction mixture
  2. concentrationwas concentrated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by silica gel chromatography (methylene chloride/methanol: 99/1 to 98/2 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-942d515f57e3447b811ce3444195e7b7
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504508B2

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