Hydrochloric Acid → 3-(5-(3-Chloro-2-(((4'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoic acid

HRID 405195Notes

Reaction equation

HRID 405195 reaction equation
[OH-].[Na+].C1COCC1.[Cl:8][C:9]1[C:10]([CH2:35][NH:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=3)=[C:39]([CH3:50])[CH:38]=2)=[C:11]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([NH:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[O:26])=[N:23][CH:24]=2)[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1.Cl>C(OCC)C.CO>[Cl:8][C:9]1[C:10]([CH2:35][NH:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:44]=[CH:45][C:46]([Cl:49])=[CH:47][CH:48]=3)=[C:39]([CH3:50])[CH:38]=2)=[C:11]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([NH:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:26])=[N:23][CH:24]=2)[CH:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71060161Ethyl 3-(5-(3-chloro-2-(((4'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 710596243-(5-(3-Chloro-2-(((4'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A 3M aqueous solution of NaOH (1.9 mL, 5.7 mmol) was added to a THF (7.6 mL) and MeOH (3.8 mL) solution of ethyl 3-(5-(3-chloro-2-(((4′-chloro-2-methyl-[1,1′-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate (2.4 g, 3.8 mmol) and the resulting homogeneous mixture was stirred at room temperature. After 30 min the resulting mixture concentrated and then acidified with 1M aqueous HCl. The resulting mixture was diluted with EtOAc and the layers were separated. The aqueous phase was extracted with EtOAc and the combined organics were washed with 4M NaCl, dried (Na2SO4), and concentrated. The resulting material was dissolved in diethyl ether, 1M diethyl ether solution of HCl (5.7 mL, 5.7 mmol) was added and the resulting precipitate was filtered, washed with diethyl ether, and dried in vacuo to yield the title compound.

Workup

  1. concentrationAfter 30 min the resulting mixture concentrated
  2. additionThe resulting mixture was diluted with EtOAc
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organics were washed with 4M NaCl
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. dissolutionThe resulting material was dissolved in diethyl ether
  9. filtrationthe resulting precipitate was filtered
  10. washwashed with diethyl ether
  11. customdried in vacuo

Sources & evidence

ORD record
ord-506ce37db2314369880cf95848bd798c
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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