Acetic Acid → Bazedoxifene Acetate

HRID 1503337Notes

Reaction equation

[C:1]([OH:4])(=[O:3])[CH3:2].[CH3:5][C:6]1[C:7]2[CH:8]=[C:9]([OH:39])[CH:10]=[CH:11][C:12]=2[N:13]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:27][CH:28]=2)[C:14]=1[C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1>C(OCC)(=O)C.C(O)C>[CH3:5][C:6]1[C:7]2[CH:8]=[C:9]([OH:39])[CH:10]=[CH:11][C:12]=2[N:13]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)=[CH:25][CH:24]=2)[C:14]=1[C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1.[CH3:2][C:1]([OH:4])=[O:3]

Participants

Conditions

Temperature: -7.5 °C

Procedure

Acetic acid (0.764 g) is charged in a mixture of ethyl acetate (35 mL) and ethanol (15 mL) and reaction mixture is cooled to −5 to −10° C. In a separate flask, crystalline bazedoxifene free base is dissolved in mixture of ethyl acetate (35 mL) and ethanol (15 mL) and the said mixture is added to the previous reaction mixture of acetic acid at −5 to −10° C. The mixture is stirred at same temperature for about 24 hours. The solid is collected by filtration and dried under vacuum at about 50° C. for 3 hours to afford the title compound.

Workup

filtrationThe solid is collected by filtration
customdried under vacuum at about 50° C. for 3 hours

Sources & evidence

ORD record: ord-a0032ef0f22e4ab1aceb017433f9edbc
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212172B2

Reaction notes

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