Hydrochloric Acid → 2-(4'-{4-[1-(2-Fluoro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-2-methyl-propionic acid

HRID 2092444Notes

Reaction equation

HRID 2092444 reaction equation
C([O:3][C:4](=[O:39])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][N:23]=[C:22]([CH3:25])[C:21]=3[NH:26][C:27]([O:29][CH:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])[CH3:31])=[O:28])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([CH3:7])[CH3:6])C.[OH-].[Li+].Cl>CO>[F:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH:30]([O:29][C:27]([NH:26][C:21]1[C:22]([CH3:25])=[N:23][O:24][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:39])=[O:3])=[CH:13][CH:12]=2)=[CH:15][CH:16]=1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 673516442-(4'-{4-[1-(2-Fluoro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 462402052-(4'-{4-[1-(2-Fluoro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-2-methyl-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4′-{4-[1-(2-Fluoro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-2-methyl-propionic acid ethyl ester (0.51 mmol) in Methanol (50 mL) was treated with lithium hydroxide (excess) as well as 1N aqueous LiOH (excess, and the reaction was stirred at room temperature. Analytical LCMS indicated that starting material was still present, so the reaction was stirred at 80° C. overnight. The mixture was neutralized with 1N HCl (20 mL) and extracted with EtOAc. The combined organic layers were washed with water, dried, and concentrated, and the residue was purified by preparative HPLC to give the title compound.

Workup

  1. stirringwas stirred at 80° C. overnight
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-160091c671df450eb7c7ad53e2149513
Source dataset
uspto-grants-2013_05
Patent number
US08440707B2

Reaction notes

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