Hydrochloric Acid → HCID 70228233, compound

HRID 566581Notes

Reaction equation

HRID 566581 reaction equation
C(C(C(C(O)=O)O)O)(O)=O.C([O:13][C:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][CH2:24][O:25][CH:26]=[C:27]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:17]1)=[O:15])C.[OH-].[Na+].[ClH:44]>C(O)C>[ClH:44].[F:41][C:38]1[CH:37]=[CH:36][C:35]([C:27]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)=[CH:26][O:25][CH2:24][CH2:23][CH2:22][N:18]2[CH2:19][CH2:20][CH2:21][C@@H:16]([C:14]([OH:15])=[O:13])[CH2:17]2)=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70230542HCID 70230542, compound

Product 1

HCID 70228233HCID 70228233, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-1-(3-((2,2-bis(4-Fluorophenyl)ethenyl)oxy)-1-propyl)-3-piperidinecarboxylic acid ethyl ester tartrate (3.8 g, 0.0065 mol, prepared similarly to the method described in Example 70) was dissolved in ethanol (25 ml) and 12 N sodium hydroxide solution (2.2 ml) was introduced at 5° C. After stirring the solution at room temperature for 4.8 h, pH of the reaction mixture was adjusted to ca. 7 with 4 N hydrochloric acid solution, and the mixture was evaporated to a residue in vacuo. Water (25 ml) was added, and the mixture was extracted with dichloromethane (3×50 ml). The combined extacts were dried (MgSO4) and evaporated to a foam, which was dissolved in toluene (1.5 ml) and warmed to 40° C. Methanol (0.27 ml) was introduced followed by chlorotrimethylsilane (0.83 ml). The product precipitated slowly, and after the suspension had been allowed to stand for 18 h at room temperature it was collected by filtration. The title compound (2.9 g, 100%) was obtained as white crystals.

Workup

  1. customthe mixture was evaporated to a residue in vacuo
  2. additionWater (25 ml) was added
  3. extractionthe mixture was extracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined extacts were dried (MgSO4)
  5. customevaporated to a foam, which
  6. dissolutionwas dissolved in toluene (1.5 ml)
  7. temperaturewarmed to 40° C
  8. additionMethanol (0.27 ml) was introduced
  9. customThe product precipitated slowly
  10. waitto stand for 18 h at room temperature
  11. filtrationit was collected by filtration

Sources & evidence

ORD record
ord-633bf0a6b82648ba90e32c5a03ec9868
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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