Hydrochloric Acid → HCID 25118869, compound

HRID 386464Notes

Reaction equation

HRID 386464 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([C:21]3[O:22][C:23]([C:26]4[N:31]=[C:30]([C:32]([O:34]C)=[O:33])[CH:29]=[CH:28][CH:27]=4)=[CH:24][N:25]=3)=[O:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:3].[Li+].[OH-].Cl>C1COCC1.O.C(Cl)Cl>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][C:19]([C:21]3[O:22][C:23]([C:26]4[N:31]=[C:30]([C:32]([OH:34])=[O:33])[CH:29]=[CH:28][CH:27]=4)=[CH:24][N:25]=3)=[O:20])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 24800869HCID 24800869, compound

Product 1

HCID 25118869HCID 25118869, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 6-(2-(3-(4′-((Dimethylamino)methyl)biphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate was dissolved in THF/H2O (3:2, 2 mL) and LiOH was added. The reaction solution was stirred at room temperature under an atmosphere of Ar for 25 min before the addition of aqueous 1 N HCl to pH 4. The reaction solution was diluted with CH2Cl2 and the organic and aqueous layers were separated. The aqueous layer was made basic to pH 8 with the addition of saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic phases were combined, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by tritration in ether to provide 6-{2-[3-(4′-Dimethylaminomethyl-biphenyl-4-yl)-propionyl]oxazol-5-yl}-pyridine-2-carboxylic acid.

Workup

  1. customthe organic and aqueous layers were separated
  2. additionThe aqueous layer was made basic to pH 8 with the addition of saturated aqueous NaHCO3
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by tritration in ether

Sources & evidence

ORD record
ord-bf22ccc8a0ce4144a67a389f6f6d3b24
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

Loading…