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

HRID 553713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553713
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

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e690d330eb9d4794bfd21047acf3ea1a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048902B2

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