Hydrochloric Acid → 5-(Carboxymethyl)-3-[3-(cyclopentyloxy)-4-methoxyphenyl]-4,5-dihydroisoxazole-5-carboxylic acid

HRID 1169849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169849
C[O:2][C:3]([C:5]1([CH2:24][C:25]([O:27]C)=[O:26])[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:6]1)=[O:4].O1CCCC1.[OH-].[Li+].Cl>O>[C:25]([CH2:24][C:5]1([C:3]([OH:4])=[O:2])[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:11]=2)[CH2:6]1)([OH:27])=[O:26]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 686864923-(3-Cyclopentyloxy-4-methoxy-phenyl)-5-methoxy carbonylmethyl-4,5-dihydro-isoxazol-5-carboxylic Acid Methyl Ester

Produkt 1

HCID 595509785-(Carboxymethyl)-3-[3-(cyclopentyloxy)-4-methoxyphenyl]-4,5-dihydroisoxazole-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of the compound obtained from step c in tetrahydrofuran (1.0 eq), was added and lithium hydroxide (5.0 eq) in water (as 5N solution). The mixture was stirred at room temperature over night. The solvent was removed under reduced pressure and the residue thus obtained was diluted with water and acidified with drops of concentrated hydrochloric acid. The organic compound was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulphate and finally concentrated under reduced pressure to afford title organic compound.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue thus obtained
  3. extractionThe organic compound was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationfinally concentrated under reduced pressure
  7. customto afford title organic compound

Quellen und Nachweise

ORD-Eintrag
ord-7781ad8aba524c7b94bd22e429429659
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825147B2

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