Hydrochloric Acid → Ridogrel

HRID 1646684Notes

Reaction equation

HRID 1646684 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[C:7](=[N:18]/[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])/[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:2]=1.[OH-].[Na+].Cl>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[C:7](=[N:18]/[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])/[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14820403HCID 14820403, compound

Product 1

HCID 5362391RidogrelYield 42.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.3 parts of ethyl (E)-5-[[[(3-pyridinyl) [3-(trifluoromethyl)phenyl]methylen]amino]oxy]pentanoate, 25 parts of a sodium hydroxide solution 1N and 20 parts of ethanol was stirred for 2.5 hours at room temperature. 25 Parts of a hydrochloric acid solution 1N were added and the ethanol layer was evaporated. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and hexane (2:1 by volume). The product was filtered off and dried, yielding 1.7 parts (42.2%) of (E)-5-[[[(3-pyridinyl)[3-(trifluoromethyl)phenyl]methylen]amino]oxy]pentanoic acid; mp. 70.3° C. (compound 63).

Workup

  1. customthe ethanol layer was evaporated
  2. extractionThe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of 2,2'-oxybispropane and hexane (2:1 by volume)
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-f7f1b6bac1c041da886b5ce04a441ec7
Source dataset
uspto-grants-1993_01
Patent number
US05180832

Reaction notes

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