N-(4-acetylphenyl)methanesulfonamide → 2-{4-[3-(4-Methanesulfonylamino-phenyl)-3-oxo-E-propenyl]-5-methoxy-2-thiophen-2-yl-phenoxy}-2-methyl-propionic acid

HRID 10721

Reaktionsgleichung

Reaktionsgleichung von HRID 10721
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:15]([C:17]1[C:29]([O:30][CH3:31])=[CH:28][C:20]([O:21][C:22]([CH3:27])([CH3:26])[C:23]([OH:25])=[O:24])=[C:19]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)[CH:18]=1)=O.C[O-].[Li+]>CN(C=O)C.CO.O>[CH3:14][S:11]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])/[CH:2]=[CH:15]/[C:17]2[C:29]([O:30][CH3:31])=[CH:28][C:20]([O:21][C:22]([CH3:27])([CH3:26])[C:23]([OH:25])=[O:24])=[C:19]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[CH:18]=2)=[CH:9][CH:8]=1)(=[O:12])=[O:13]

Komponenten

7

Edukt 3

HCID 684083N-(4-acetylphenyl)methanesulfonamideHCID 4177230Lithium methanolateHCID 219809942-(4-Formyl-5-methoxy-2-thiophen-2-yl-phenoxy)-2-methyl-propionic acid

Produkt 1

HCID 219811072-{4-[3-(4-Methanesulfonylamino-phenyl)-3-oxo-E-propenyl]-5-methoxy-2-thiophen-2-yl-phenoxy}-2-methyl-propionic acidAusbeute 15,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(4-acetyl-phenyl)-methanesulfonamide (Ex-100A, 279.6 mg, 1.31 mmol) and 2-(4-formyl-5-methoxy-2-thiophen-2-yl-phenoxy)-2-methyl-propionic acid (Ex-47D, 400 mg, 1.20 mmol) in DMF (5.25 mL) and MeOH (2.25 mL) was treated with lithium methoxide (182.2 mg, 4.8 mmol) and stirred for 5 hours at room temp. under nitrogen atmosphere. The reaction mixture was diluted with water (25 mL) which was then extracted with isopropyl acetate (2×50 mL). The aqueous portion was collected and acidified to a pH of 3 with 3N HCl. The aqueous solution was then extracted with isopropyl acetate (2×50 mL). The organic was collected, dried over sodium sulfate, and concentrated to a green solid. Attempted to recrystallize crude material from ethanol/hexanes; however, this mixture was concentrated and stirred with ethyl acetate (3 mL) to give 95.6 mg (14%) of the title compound as a yellow solid, mp 181–183° C. 1H-NMR (DMSO-d6) δ 10.31 (br s, 1H), 8.24 (s, 1H), 8.12 (d, 2H), 7.95 (d, 1H), 7.87 (d, 1H), 7.67 (d, 1H), 7.50 (d, 1H), 7.30 (d, 2H), 7.09 (t, 1H), 6.45 (s, 1H), 3.81 (s, 3H), 3.08 (s, 3H), 1.65 (s, 6H). MS m/z=516 ([M+H]+, 100%). HRMS m/z: calc. 516.1150, found 516.1165.

Aufarbeitung

  1. extractionwas then extracted with isopropyl acetate (2×50 mL)
  2. customThe aqueous portion was collected
  3. extractionThe aqueous solution was then extracted with isopropyl acetate (2×50 mL)
  4. customThe organic was collected
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a green solid
  7. customAttempted to recrystallize crude material from ethanol/hexanes
  8. concentrationhowever, this mixture was concentrated
  9. stirringstirred with ethyl acetate (3 mL)

Quellen und Nachweise

ORD-Eintrag
ord-36f24c76b431434481f775654182115c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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