Tetrahydrofuran → 3-(5-(5-Methoxy-2-(((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoic acid

HRID 405167Notes

Reaction equation

HRID 405167 reaction equation
[OH-].[Na+].C1COCC1.[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:32][NH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=3)=[CH:36][CH:35]=2)=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])=[O:23])=[N:20][CH:21]=2)[CH:15]=1>CO>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:32][NH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:41]=[CH:42][C:43]([C:46]([F:48])([F:49])[F:47])=[CH:44][CH:45]=3)=[CH:36][CH:35]=2)=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:23])=[N:20][CH:21]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71059803Ethyl 3-(5-(5-methoxy-2-(((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Product 1

HCID 710600713-(5-(5-Methoxy-2-(((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3M aqueous solution of NaOH (0.15 mL, 0.44 mmol) was added to a THF (1.8 mL) and MeOH (2 mL) solution of ethyl 3-(5-(5-methoxy-2-(((4′-(trifluoromethyl)-[1,1′-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate (85 mg, 0.15 mmol) and the resulting mixture was stirred at room temperature. After 2 h the resulting mixture was concentrated in vacuo, suspended in water, and acidified with 2 M HCl. The resulting precipitate was filtered off and dried in vacuo to yield the title compound.

Workup

  1. concentrationAfter 2 h the resulting mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1b3abd4045c345419d92ee0cd4c0373f
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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