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

HRID 748947노트

반응식

HRID 748947 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 685175026-(4-Methanesulfonyl-3-methoxy-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol수율 76.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eac02a64880b48738a88f0f46f5401e0
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399867B2

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