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

HRID 405142Notes

Reaction equation

HRID 405142 reaction equation
[OH-].[Na+].C1COCC1.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][N:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=3)=[CH:36][CH:35]=2)[CH3:33])=[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][N:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=3)=[CH:36][CH:35]=2)[CH3:33])=[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 71059954Ethyl 3-(5-(5-chloro-2-(((4'-chloro-[1,1'-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinamido)propanoate

Product 1

HCID 710600993-(5-(5-Chloro-2-(((4'-chloro-[1,1'-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3M aqueous solution of NaOH (0.29 mL, 0.88 mmol) was added to a THF (2 mL) and MeOH (1 mL) solution of ethyl 3-(5-(5-chloro-2-(((4′-chloro-[1,1′-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinamido)propanoate (165 mg, 0.29 mmol) and the resulting homogeneous mixture was stirred at room temperature. After 16 h the 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 mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-3d6432b69c164334a2edd5084d930d50
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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