Sodium Hydroxide → 3-(5-(2-(((4'-Chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-4,5-difluorophenyl)picolinamido)propanoic acid

HRID 405212Notes

Reaction equation

HRID 405212 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=3[C:26]3[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])=[O:33])=[N:30][CH:31]=3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=3[C:26]3[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[N:30][CH:31]=3)=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71060105Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-4,5-difluorophenyl)picolinamido)propanoate

Product 1

HCID 710600683-(5-(2-(((4'-Chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-4,5-difluorophenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3M aqueous solution of NaOH (0.34 mL, 1.03 mmol) was added to a THF solution (1.1 mL) of ethyl 3-(5-(2-(((4′-chloro-[1,1′-biphenyl]-4-yl)amino)methyl)-4,5-difluorophenyl)picolinamido)propanoate (115 mg, 0.21 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture was concentrated and purified via HPLC to yield the title compound.

Workup

  1. concentrationAfter 16 h the resulting mixture was concentrated
  2. custompurified via HPLC

Sources & evidence

ORD record
ord-c36c583e5e044400b165c080dd48be75
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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