Hydrochloric Acid → 3-(5-(2-((4'-Chloro-2'-methyl-[1,1'-biphenyl]-4-yl)carbamoyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoic acid

HRID 405233Notes

Reaction equation

HRID 405233 reaction equation
[Li+].[OH-].C1COCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:25]=3[C:34]3[CH:35]=[CH:36][C:37]([C:40]([NH:42][CH2:43][CH2:44][C:45]([O:47]CC)=[O:46])=[O:41])=[N:38][CH:39]=3)=[O:23])=[CH:17][CH:16]=2)=[C:11]([CH3:50])[CH:10]=1.Cl>CCOC(C)=O.O.CO>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:31])[F:33])=[CH:26][C:25]=3[C:34]3[CH:35]=[CH:36][C:37]([C:40]([NH:42][CH2:43][CH2:44][C:45]([OH:47])=[O:46])=[O:41])=[N:38][CH:39]=3)=[O:23])=[CH:17][CH:16]=2)=[C:11]([CH3:50])[CH:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 71060022Ethyl 3-(5-(2-((4'-chloro-2'-methyl-[1,1'-biphenyl]-4-yl)carbamoyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 710601103-(5-(2-((4'-Chloro-2'-methyl-[1,1'-biphenyl]-4-yl)carbamoyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1M aqueous solution of LiOH (1.0 mL, 1.0 mmol) was added to a THF (2.0 mL) and MeOH (0.5 mL) solution of ethyl 3-(5-(2-((4′-chloro-2′-methyl-[1,1′-biphenyl]-4-yl)carbamoyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate (85 mg, 0.14 mmol) and the resulting mixture was stirred at room temperature. After 1 h the resulting mixture was neutralized with 2M aqueous HCl, diluted with EtOAc and water and the layers were separated. The aqueous layer was extracted with EtOAc and the combined extracts were dried (Na2SO4), and concentrated. The title compound was re-solidified from CH2Cl2/heptane (ca. 1/19) and dried in vacuo.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e9b872e1eb9f48cf97f28d6fb155d3da
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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