Ethanol → Bazedoxifene Acetate

HRID 1503320Notes

Reaction equation

HRID 1503320 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.[CH2:36]([OH:38])[CH3:37].C([O:42]C(C)C)(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.[CH3:37][C:36]([OH:42])=[O:38]

Participants

5

Reactant 3

HCID 702EthanolHCID 7914Diisopropyl EtherHCID 154257Bazedoxifene

Product 1

HCID 154256Bazedoxifene AcetateYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bazedoxifene free base (500 mg) and ethanol (10 mL) are mixed and stirred for about 10 minutes. Acetic acid (2 mL) is added slowly through a dropper and the mixture is stirred for 10 minutes at room temperature to produce a clear solution. Diisopropyl ether (30 mL) is added and the mixture is stirred overnight for solid formation. The solid is collected by filtration and washed sequentially with diisopropyl ether (5 mL) and water (5 mL), then is suction dried for 5 minutes. The obtained wet solid is further dried under vacuum at 70° C. for about 4-5 hours to afford 420 mg (85% yield) of crystalline bazedoxifene acetate Form D.

Workup

  1. stirringthe mixture is stirred for 10 minutes at room temperature
  2. customto produce a clear solution
  3. stirringthe mixture is stirred overnight for solid formation
  4. filtrationThe solid is collected by filtration
  5. washwashed sequentially with diisopropyl ether (5 mL) and water (5 mL)
  6. customdried for 5 minutes
  7. customThe obtained wet solid is further dried under vacuum at 70° C. for about 4-5 hours

Sources & evidence

ORD record
ord-effabfa25c5b43988d5e476fc81e145f
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Reaction notes

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