Dimethylformamide → HCID 19611486, Verbindung

A mixture of 5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-hydroxy-3-(6-methoxy-2-benzothiazolylmethoxy)benzanilide (301 mg, 0.48 mmol), potassium carbonate (135 mg, 0.98 mmol), ethyl bromoacetate (81 mg, 0.49 mmol) and dimethylformamide (5 ml) was stirred at room temperature for 12 hours. Water was added to the reaction solution and the product formed was extracted with ethyl acetate. The extract was washed with water and brine in that order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Tetrahydrofuran (2 ml), methanol (1 ml) and 1 N sodium hydroxide were added to the resulting residue and the mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated, and water was added to the resulting residue, and the mixture was adjusted to pH 3 with 10% citric acid aqueous solution. Thereafter, the solid material formed was collected by filtration and washed with acetonitrile to give 4-[3-(4-chlorophenylsulfonyl)propyl]-2-[3-[(6-methoxy-2-benzothiazolyl)methoxy]benzoylamino]phenoxyacetic acid (145 mg, 0.21 mmol, 44%).

1. customthe product formed
2. extractionwas extracted with ethyl acetate
3. washThe extract was washed with water and brine in that order
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. additionTetrahydrofuran (2 ml), methanol (1 ml) and 1 N sodium hydroxide were added to the resulting residue
7. stirringthe mixture was stirred at room temperature for 12 hours
8. concentrationThe reaction solution was concentrated
9. additionwater was added to the resulting residue
10. customThereafter, the solid material formed
11. filtrationwas collected by filtration
12. washwashed with acetonitrile

ORD-Eintrag

ord-a30b859d9f594238ba7d1dde5c4b0a55

Quelldatensatz

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05981559