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

HRID 405125Notes

Reaction equation

HRID 405125 reaction equation
[OH-].[Na+].C1COCC1.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][NH:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=3[Cl:46])=[CH:35][CH:34]=2)=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[O:22])=[N:19][CH:20]=2)[CH:14]=1>CO>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][NH:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=3[Cl:46])=[CH:35][CH:34]=2)=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[N:19][CH:20]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71059822Ethyl 3-(5-(5-chloro-2-(((2',4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Product 1

HCID 710599813-(5-(5-Chloro-2-(((2',4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3M aqueous solution of NaOH (7.5 mL, 22.6 mmol) was added to a THF (40 mL) and MeOH (20 mL) solution of ethyl 3-(5-(5-chloro-2-(((2′,4′-dichloro-[1,1′-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate (6.6 g, 11.3 mmol) and the resulting homogeneous 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-98190f2b9bbf4527984c678f8c3c5893
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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