tert-Butyl methyl ether → Bazedoxifene Acetate

HRID 1503318

Reaction equation

HRID 1503318 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.[C:36]([O:40]C)([CH3:39])(C)C>C(O)(=O)C>[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.[CH3:39][C:36]([OH:40])=[O:17]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 154257Bazedoxifene

Product 1

HCID 154256Bazedoxifene Acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bazedoxifene free base (400 mg) and methyl tert-butyl ether (30 mL) are mixed and stirred for about 10 minutes. Acetic acid (0.17 g) is added slowly through a dropper and the mixture is stirred overnight for solid formation. The solid is collected by filtration to afford 250 mg of crystalline bazedoxifene acetate Form D.

Workup

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

Sources & evidence

ORD record
ord-b6ac894438f44dbcbe6c1b754deae012
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Linked notes

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