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Ethanol → Bilastine

HRID 384012
Notes
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Reaction equation

HRID 384012 reaction equation
C[O:2][C:3](=[O:35])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21]3[N:25]([CH2:26][CH2:27][O:28][CH2:29][CH3:30])[C:24]4[CH:31]=[CH:32][CH:33]=[CH:34][C:23]=4[N:22]=3)[CH2:17][CH2:16]2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[Na+].C(O)C.O>C(O)CCC.C(OC(=O)C)C.C(O)(=O)C>[CH2:29]([O:28][CH2:27][CH2:26][N:25]1[C:24]2[CH:31]=[CH:32][CH:33]=[CH:34][C:23]=2[N:22]=[C:21]1[CH:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][C:10]2[CH:9]=[CH:8][C:7]([C:4]([CH3:5])([CH3:6])[C:3]([OH:35])=[O:2])=[CH:12][CH:11]=2)[CH2:16][CH2:17]1)[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 45257628Bilastine Ester

Product 1

HCID 185460BilastineYield 90%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent
HCID 263
1-Butanol
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

In a reaction vessel, 2-[4-(2-{4-[1-(2-ethoxy-ethyl)-1H-benzoimidazol-2-yl]-piperidin-1-yl}-ethyl)-phenyl]-2-methyl-propionic acid methylester (2.3 g) prepared in the Example 14, sodium hydroxide (0.6 g) and ethylalcohol (13 mL) were introduced, and the mixture was reacted at 50-55° C. for 3 hours. Distilled water (20 mL) was added thereto, and acetic acid was added to control the pH to 7. Ethylacetate (50 mL) was added thereto, and the mixture was stirred to separate a layer. The separated organic layer was condensed under reduced pressure. And, butanol (9 mL) was added thereto, and dissolved by'heating. And then, it was cooled to precipitate crystals, and the crystals were filtered under reduced pressure to obtain 2-[4-(2-{4-[1-(2-ethoxy-ethyl)-1H-benzoimidazol-2-yl]-piperidin-1-yl}ethyl)-phenyl]-2-methyl-propionic acid (2.0 g, yield 90%, HPLC purity 99% or more).

Workup

  1. additionwere introduced
  2. customthe mixture was reacted at 50-55° C. for 3 hours
  3. customto separate a layer
  4. customcondensed under reduced pressure
  5. dissolutiondissolved
  6. temperatureAnd then, it was cooled
  7. customto precipitate crystals
  8. filtrationthe crystals were filtered under reduced pressure

Sources & evidence

ORD record
ord-f736c90c997043b7b15620ce76f24237
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367704B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes