Hydrochloric Acid → 3-(5-(3-Chloro-5-(((4'-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoic acid

HRID 405270Notes

Reaction equation

HRID 405270 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])=[O:32])=[N:29][CH:30]=2)[CH:7]=[C:8]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH:9]=1.Cl>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[O:32])=[N:29][CH:30]=2)[CH:7]=[C:8]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71060021Ethyl 3-(5-(3-chloro-5-(((4'-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Product 1

HCID 710600783-(5-(3-Chloro-5-(((4'-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A 1M aqueous solution of NaOH (0.47 mL, 0.47 mmol) was added to a THF solution (5 mL) of ethyl 3-(5-(3-chloro-5-(((4′-fluoro-[1,1′-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate (100 mg, 0.19 mmol) and the resulting mixture was heated to 40° C. After 4 h the resulting mixture was acidified with 1 M HCl and the aqueous phase was extracted with EtOAc. The combined organics were washed with water, dried (Na2SO4), and concentrated to yield the title compound.

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. washThe combined organics were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-83e44e24f5bb47d284f0b5247b5995bc
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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