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

HRID 405273Notes

Reaction equation

HRID 405273 reaction equation
[OH-].[Na+].C1COCC1.[Cl:8][C:9]1[CH:10]=[C:11]([C:31]2[CH:32]=[CH:33][C:34]([C:37]([NH:39][CH2:40][CH2:41][C:42]([O:44]CC)=[O:43])=[O:38])=[N:35][CH:36]=2)[CH:12]=[C:13]([C:15](=[O:30])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[CH:14]=1.Cl>CO>[Cl:8][C:9]1[CH:10]=[C:11]([C:31]2[CH:32]=[CH:33][C:34]([C:37]([NH:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[O:38])=[N:35][CH:36]=2)[CH:12]=[C:13]([C:15](=[O:30])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71059931Ethyl 3-(5-(3-chloro-5-((4'-chloro-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)picolinamido)propanoate

Product 1

HCID 710599583-(5-(3-Chloro-5-((4'-chloro-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1M aqueous solution of NaOH (2.0 mL, 2.0 mmol) was added to a THF (1 mL) and MeOH (5 mL) solution of ethyl 3-(5-(3-chloro-5-((4′-chloro-[1,1′-biphenyl]-4-yl)carbamoyl)phenyl)picolinamido)propanoate (40 mg, 0.07 mmol) and the resulting mixture was stirred at room temperature. After 16 h the mixture was acidified with 2 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-ed9003c9c01f46d0a38d5687fcfa29ae
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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