Hexane → 3-[[3-[Oxo-(2-thienylmethylamino)methyl]-2-quinolyl]thio]propanoic acid methyl ester

HRID 1949168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1949168
[CH3:1][O:2][C:3](=[O:7])[CH2:4][CH2:5][SH:6].CC([O-])(C)C.[K+].Cl[C:15]1[C:24]([C:25]([NH:27][CH2:28][C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[O:26])=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1.CCCCCC>CN(C=O)C>[CH3:1][O:2][C:3](=[O:7])[CH2:4][CH2:5][S:6][C:15]1[C:24]([C:25](=[O:26])[NH:27][CH2:28][C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 18050Methyl 3-mercaptopropionateHCID 23665647Potassium tert-butoxideHCID 866453382-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide

Produkt 1

HCID 594862173-[[3-[Oxo-(2-thienylmethylamino)methyl]-2-quinolyl]thio]propanoic acid methyl esterAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 361 mg (3.0 mmol) 3-mercaptopropionic acid methyl ester in DMF (18 ml) was cooled to 0° C. and mixed with 336.6 mg (3.0 mmol) potassium tert-butylate and stirred for 10 min. Then 908 mg (3.0 mmol) 2-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide (precursor VVV01) were added and the reaction solution was then heated slowly to 50° C. and stirred for 16 h at this temperature. It was then diluted with EE and washed with a saturated aqueous NH4Cl solution. The aqueous phase was extracted with EE. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 4:1) with the residue yielded 614 mg (1.6 mmol, 53%) 3-[[3-[oxo-(2-thienylmethylamino)methyl]-2-quinolyl]thio]propanoic acid methyl ester. MS: m/z 387.1 [M+H]+.

Aufarbeitung

  1. stirringstirred for 16 h at this temperature
  2. additionIt was then diluted with EE
  3. washwashed with a saturated aqueous NH4Cl solution
  4. extractionThe aqueous phase was extracted with EE
  5. washThe combined organic phases were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to small volume under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5e958d3f83624a51bace6aa76ab56a90
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399673B2

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