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

HRID 405262Notes

Reaction equation

HRID 405262 reaction equation
[OH-].[Na+].C1COCC1.[Cl:8][C:9]1[CH:14]=[C:13]([NH:15][CH2:16][C:17]2[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][C:20]([C:26]([F:29])([F:28])[F:27])=[CH:19][C:18]=2[C:30]2[CH:31]=[CH:32][C:33]([C:36]([NH:38][CH2:39][CH2:40][C:41]([O:43]CC)=[O:42])=[O:37])=[N:34][CH:35]=2)[CH:12]=[CH:11][C:10]=1[C:46]1[CH:51]=[CH:50][C:49]([C:52]([F:55])([F:54])[F:53])=[CH:48][C:47]=1[CH3:56].Cl>CO>[Cl:8][C:9]1[CH:14]=[C:13]([NH:15][CH2:16][C:17]2[C:22]([CH:23]([CH3:24])[CH3:25])=[CH:21][C:20]([C:26]([F:28])([F:29])[F:27])=[CH:19][C:18]=2[C:30]2[CH:31]=[CH:32][C:33]([C:36]([NH:38][CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[O:37])=[N:34][CH:35]=2)[CH:12]=[CH:11][C:10]=1[C:46]1[CH:51]=[CH:50][C:49]([C:52]([F:55])([F:53])[F:54])=[CH:48][C:47]=1[CH3:56]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86674292Ethyl 3-(5-(2-(((2-chloro-2'-methyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 866742933-(5-(2-(((2-Chloro-2'-methyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3M aqueous NaOH solution (0.04 mL, 0.11 mmol) was added to a THF (2.0 mL) and MeOH (1.0 mL) solution of ethyl 3-(5-(2-(((2-chloro-2′-methyl-4′-(trifluoromethyl)-[1,1′-biphenyl]-4-yl)amino)methyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (13 mg, 0.02 mmol) and the resulting mixture was stirred at room temperature. After 2 h the resulting mixture was acidified with 1N aqueous HCl and extracted with EtOAc. The combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-dc3567e0a98f438c96add42999726cc2
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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