Water → Bazedoxifene

HRID 1503310

반응식

HRID 1503310 반응식
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:15][CH:14]=2)[C:3]=1[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1.Cl.ClCCl.O>C(N(CC)CC)C>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[N:4]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:17][CH:18]=2)[C:3]=1[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 6344DichloromethaneHCID 9936012Bazedoxifene HCl

생성물 1

HCID 154257Bazedoxifene수율 73.27%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

Bazedoxifene hydrochloride (5 g), dichloromethane (75 mL), and water (50 mL) are mixed and triethylamine (4 mL) is slowly added to obtain a pH range of 9.5-10.5 of the aqueous phase. The layers are separated and the aqueous layer is extracted with dichloromethane (2×25 mL). The organic layers are combined followed by addition of water (50 mL), at which point pH of the aqueous phase is about 10.4. To this mixture, a solution of 5% acetic acid (75 mL) is slowly added until the pH is about 9, at which point a crystalline solid forms. The solid is collected by filtration, washed with dichloromethane (25 mL), and dried under vacuum at 50° C. to afford crystalline bazedoxifene free base in 73.27% yield (HPLC purity 99.67%).

후처리

  1. customto obtain a pH range of 9.5-10.5 of the aqueous phase
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with dichloromethane (2×25 mL)
  4. additionThe organic layers are combined followed by addition of water (50 mL), at which point pH of the aqueous phase
  5. additionTo this mixture, a solution of 5% acetic acid (75 mL) is slowly added until the pH is about 9, at which point a crystalline solid forms
  6. filtrationThe solid is collected by filtration
  7. washwashed with dichloromethane (25 mL)
  8. customdried under vacuum at 50° C.

출처 및 근거

ORD 기록
ord-1180137dceeb45d28e2ea281e118885b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212172B2

연결된 노트

불러오는 중…