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

HRID 405173Notes

Reaction equation

HRID 405173 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=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:13][C:12]=2[F:42])[CH:7]=[CH:8][C:9]=1[Cl:10]>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=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:13][C:12]=2[F:42])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71059960Ethyl 3-(5-(2-(((3',4'-dichloro-2-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-fluorophenyl)picolinamido)propanoate

Product 1

HCID 710599513-(5-(2-(((3',4'-Dichloro-2-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-fluorophenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3M aqueous solution of NaOH (0.10 mL, 0.31 mmol) was added to a THF solution (3 mL) of ethyl 3-(5-(2-(((3′,4′-dichloro-2-fluoro-[1,1′-biphenyl]-4-yl)amino)methyl)-5-fluorophenyl)picolinamido)propanoate (60 mg, 0.10 mmol) and the resulting mixture was stirred at room temperature. After 16 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 16 h the resulting mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-3bd06ed5ce4148ecbf47efab83607e43
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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