Asulam → (S)-methyl 4-(2-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutanamido)phenylsulfonylcarbamate

HRID 333691

Reaktionsgleichung

Reaktionsgleichung von HRID 333691
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:15])[O:13][CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[Al](C)C.[Cl:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]([C@H:31]1[CH2:35][CH2:34][O:33][C:32]1=[O:36])[CH2:26][CH2:25][CH2:24]2>C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]([C@@H:31]([CH2:35][CH2:34][OH:33])[C:32]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:15])[O:13][CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1)=[O:36])[CH2:26][CH2:25][CH2:24]2

Komponenten

5

Edukt 3

HCID 18752AsulamHCID 16682925TrimethylaluminumHCID 59465621(S)-3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)dihydrofuran-2(3H)-one

Produkt 1

HCID 59850055(S)-methyl 4-(2-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutanamido)phenylsulfonylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirring suspension of the methyl 4-aminophenylsulfonylcarbamate (111 mg, 0.48 mmol) and CH2Cl2 (1 mL) under N2, at 0° C., was added trimethylaluminum (0.24 mL, 0.48 mmol) dropwise over 20 minutes. The solution was stirred at ambient temperature for 30 minutes. The solution was cooled to 0° C. followed by the dropwise addition of (S)-3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)dihydrofuran-2(3H)-one (100 mg, 0.40 mmol) in CH2Cl2 (1.0 mL) over 30 minutes. The solution was stirred at ambient temperature for 19 h. The solution was cooled to 0° C. and quenched by slow addition of aqueous 1.0 M HCl. The organic portion was washed with 1.0 N aqueous HCl (2×1.0 mL) and evaporated to dryness under reduced pressure. The crude product of (R)-methyl 4-(2-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutanamido)phenylsulfonylcarbamate was used without purification in the next step.

Aufarbeitung

  1. temperatureThe solution was cooled to 0° C.
  2. stirringThe solution was stirred at ambient temperature for 19 h
  3. temperatureThe solution was cooled to 0° C.
  4. customquenched by slow addition of aqueous 1.0 M HCl
  5. washThe organic portion was washed with 1.0 N aqueous HCl (2×1.0 mL)
  6. customevaporated to dryness under reduced pressure
  7. customThe crude product of (R)-methyl 4-(2-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutanamido)phenylsulfonylcarbamate was used without purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-e1e090065e6443d581f9afb3de90662b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883766B2

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