Lithium Hydroxide → 2-[4-methoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

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Reaktionsgleichung

C[O:2][C:3]([C:5]1([NH:14][C:15](=[O:34])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[OH-].[Li+]>O1CCOCC1>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:5]2([C:3]([OH:4])=[O:2])[CH2:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13]2)=[O:34])=[CH:17][C:18]=1[O:24][CH2:25][CH2:26][C:27]1[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

The compound of example 13 (1.92 g, 4.18 mmol) was dissolved in dioxane (40 ml), lithium hydroxide (10 ml, 1 M solution in water) was added and the mixture was stirred for 30 min at 60° C. The mixture was partitioned between 2 N hydrochloric acid and EA, the aqueous phase extracted with EA, and the combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. The residue was stirred overnight in EA, filtered, and the crystals were dried in vacuo to give 1.35 g of the title compound.

Aufarbeitung

customThe mixture was partitioned between 2 N hydrochloric acid and EA
extractionthe aqueous phase extracted with EA
washthe combined organic extracts were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated to dryness
stirringThe residue was stirred overnight in EA
filtrationfiltered
customthe crystals were dried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-5e95d342ebd24ee7a81ec3faf984f7ec
Quelldatensatz: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08445530B2

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