4-Methylmorpholine → 1-[[4-(1,1-Dimethylethyl)phenyl]sulfonyl]-1,2,3,4-tetrahydro-2-quinolinylcarboxylic acid, methyl ester

HRID 253156

Reaktionsgleichung

Reaktionsgleichung von HRID 253156
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)=[O:4].[CH3:15][C:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)([CH3:18])[CH3:17].CN1CCOCC1>C(#N)C>[CH3:18][C:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][CH2:14][CH:5]2[C:3]([O:2][CH3:1])=[O:4])(=[O:26])=[O:27])=[CH:21][CH:20]=1)([CH3:15])[CH3:17]

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 2736972Methyl 1,2,3,4-tetrahydroquinoline-2-carboxylate

Produkt 1

HCID 866123001-[[4-(1,1-Dimethylethyl)phenyl]sulfonyl]-1,2,3,4-tetrahydro-2-quinolinylcarboxylic acid, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution is prepared of 300 mg (1.32 mmol) of 1,2,3,4-tetrahydro-2-quinolinylcarboxylic acid methyl ester in 20 ml of acetonitrile and, at ambient temperature, 309 mg (1.32 mmol) of 4-(1,1-dimethylethyl)-benzenesulfonyl chloride are added, then 0.29 ml (2.64 mmol) of N-methylmorpholine. The reaction mixture is agitated for 18 hours with solvent reflux and then concentrated under reduced pressure. The evaporation residue is collected in 50 ml of ethyl acetate and washed with a solution of hydrochloric acid 1 N then by a solution of saturated sodium bicarbonate. The organic phase is dried on magnesium sulfate and concentrated under reduced pressure. The raw product is purified by silica gel chromatography eluting with the help of a methylcyclohexane/ethyl acetate mixture (99/1 then 95/5; v/v). In this way the expected product is obtained in the form of a white solid (yield=22%).

Aufarbeitung

  1. temperaturereflux
  2. concentrationconcentrated under reduced pressure
  3. customThe evaporation residue is collected in 50 ml of ethyl acetate
  4. washwashed with a solution of hydrochloric acid 1 N
  5. customThe organic phase is dried on magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe raw product is purified by silica gel chromatography
  8. washeluting with the help of a methylcyclohexane/ethyl acetate mixture (99/1

Quellen und Nachweise

ORD-Eintrag
ord-fffc2a376c534d85b748f79d537bc251
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872021B2

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