Sodium Bicarbonate → 6-(4-Methanesulfonyl-3-methoxy-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol

HRID 748947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748947
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([O:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:28][CH:27]=3)=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([O:21]C(=O)C)[CH:15]=[CH:14]3)=[CH:7][C:6]=1[O:41][CH3:42])(=[O:4])=[O:3].C([O-])(O)=O.[Na+]>CO>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([O:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:28][CH:27]=3)=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([OH:21])[CH:15]=[CH:14]3)=[CH:7][C:6]=1[O:41][CH3:42])(=[O:4])=[O:3]

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 59751425Acetic acid 6-(4-methanesulfonyl-3-methoxy-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester

Produkt 1

HCID 685175026-(4-Methanesulfonyl-3-methoxy-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-olAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Dissolve the compound of Example 81 (210 mg, 0.36 mmol) in MeOH (4 mL). Add NaHCO3 (60 mg, 0.72 mmol) and stir the reaction mixture for 12 hours at room temperature. Filter and remove the solvent under reduced pressure. Purify the residue by flash column chromatography (silica gel, 2 to 10% MeOH—NH4OH (10/1, v/v)/CH2Cl2) to give 150 mg of 6-(4-methanesulfonyl-3-methoxy-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol (75%). Dissolve the free base (150 mg, 0.27 mm iol) in CH2Cl2 (5 mL) and cool to −78° C. Add 2M HCl in diethyl ether (0.2 mL) and stir the solution for 5 minutes. Remove the solvent under reduced pressure to give a solid. Dry the solid at room temperature overnight in vacuo to give 140 mg of the title compound (87%): mass spectrum (ion spray): m/z=548.1 (M+H—HCl).

Aufarbeitung

  1. filtrationFilter
  2. customremove the solvent under reduced pressure
  3. customPurify the residue by flash column chromatography (silica gel, 2 to 10% MeOH—NH4OH (10/1

Quellen und Nachweise

ORD-Eintrag
ord-eac02a64880b48738a88f0f46f5401e0
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399867B2

Notizen zur Reaktion

Wird geladen…