HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethanol → Bilastine

HRID 451236
Notes
Print preview

Reaction equation

HRID 451236 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□ 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□ for 3 hours
  3. customto separate a layer
  4. customcondensed under reduced pressure
  5. dissolutiondissolved
  6. temperatureby heating
  7. temperatureAnd then, it was cooled
  8. customto precipitate crystals
  9. filtrationthe crystals were filtered under reduced pressure

Sources & evidence

ORD record
ord-df4022744de849e6ae6130c32a81c108
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08487106B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes