Acetic Acid → Bazedoxifene Acetate

HRID 1503319Notes

Reaction equation

[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]([OH:35])[CH:6]=[CH:7][C:8]=2[N:9]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:23][CH:24]=2)[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1.C1(C)C=CC=CC=1.[C:43]([OH:46])(=[O:45])[CH3:44]>>[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]([OH:35])[CH:6]=[CH:7][C:8]=2[N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:21][CH:20]=2)[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1.[CH3:44][C:43]([OH:46])=[O:45]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 1140Toluene

HCID 154257Bazedoxifene

Product 1

HCID 154256Bazedoxifene AcetateYield 44.3%

Procedure

Bazedoxifene free base (400 mg) and toluene (30 mL) are mixed and stirred for about 10 minutes. Acetic acid (0.17 g) is added slowly through a dropper and the mixture stirred overnight for solid formation. The solid is collected by filtration to afford 200 mg of crystalline bazedoxifene acetate Form D.

Workup

stirringthe mixture stirred overnight for solid formation
filtrationThe solid is collected by filtration

Sources & evidence

ORD record: ord-694e210bcd174ae888593a0710253c2e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212172B2

Reaction notes

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