Reaktion #79721

Reaktionsgleichung

[9-benzyl-5-carbamoyl-1-methylcarbazol-4-yl]oxyacetic acid methyl ester

sodium hydroxide

→

title compound

Ausbeute 87.4%

[9-benzyl-5-carbamoyl-1-methylcarbazol-4-yl]oxyacetic acid

Ausbeute 87.4%

Lösungsmittel

tetrahydrofuran

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   Sonstigethe residue was partitioned between 1:1 ethyl acetate/tetrahydrofuran and 0.2 N HCl solution
3. 3
   ExtraktionAfter another extraction with 1:1 ethyl acetate/tetrahydrofuran
4. 4
   Waschenthe extracts were washed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated

Vorschrift

A slurry of 32 mg (0.0795 mmol) of [9-benzyl-5-carbamoyl-1-methylcarbazol-4-yl]oxyacetic acid methyl ester in 1 ml of tetrahydrofuran and 3.5 ml of methanol was treated with 0.3 ml of an aqueous 2 N sodium hydroxide solution and stirred overnight at room temperature. The solvent was evaporated and the residue was partitioned between 1:1 ethyl acetate/tetrahydrofuran and 0.2 N HCl solution. After another extraction with 1:1 ethyl acetate/tetrahydrofuran, the extracts were washed with brine, dried over magnesium sulfate and concentrated to afford (27 mg) of the title compound. mp. 253-254° C. ESIMS m/e 389 (M++1), 387 (M+−1) NMR (300 MHz, d6-DMSO): δ12.83 (br, 1H); 7.75 (br, 1H); 7.53 (d, J=8.2, 1H); 7.41-7.34 (m, 2H); 7.28-7.17 (m, 3H); 7.07 (m, 2H); 6.90 (d, J=7.2, 2H); 6.49 (d, J=8.1, 1H); 5.89 (s, 2H); 4.79 (s, 2H); 2.52 (s, 3H).

Quelle