Methanol → 2-[4-[4-[3-methyl-4-[[(1R)-1-phenylethoxy]carbonylamino]-1,2-oxazol-5-yl]phenyl]phenyl]acetic acid

HRID 2092459Notes

Reaction equation

HRID 2092459 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:22][N:21]=[C:20]([CH3:23])[C:19]=3[NH:24][C:25]([O:27][C@@H:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])=[O:26])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)C.CO.[OH-].[Li+]>O>[CH3:23][C:20]1[C:19]([NH:24][C:25]([O:27][C@@H:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH3:29])=[O:26])=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:36])=[O:3])=[CH:11][CH:10]=3)=[CH:13][CH:14]=2)[O:22][N:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67352169[4'-[3-Methyl-4-[[[((R)-1-phenylethyl)oxy]carbonyl]amino]isoxazol-5-yl]biphenyl-4-yl]acetic acid ethyl ester

Product 1

HCID 462139492-[4-[4-[3-methyl-4-[[(1R)-1-phenylethoxy]carbonylamino]-1,2-oxazol-5-yl]phenyl]phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of {4′-[3-methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-4-yl}-acetic acid ethyl ester (24 g, 49 mmol) in 3:1 MeOH:H2O (300 mL) was added lithium hydroxide (8.3 g, 198 mmol), and the reaction was stirred at room temperature overnight. The mixture was acidified and partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated to give the title compound. Mass spec. data (M+H)=457.

Workup

  1. custompartitioned between EtOAc and H2O
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layers were washed with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b66e28dda314f5081d3ca622350b92e
Source dataset
uspto-grants-2013_05
Patent number
US08440707B2

Reaction notes

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