Lithium Hydroxide → 6-(Benzenesulphonylmethyl)-2-(2-t-butoxyaminoethoxy)-3-ethylbenzoic acid

HRID 2177770Notizen

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

A mixture of methyl 6-(benzenesulphonylmethyl)-2-(2-t-butoxycarbonylaminoethoxy)-3-ethylbenzoate (Intermediate 108, 0.125 g), and lithium hydroxide (0.066 g) in dioxane (1.4 ml) and water (0.4 ml) was stirred and heated in the microwave at 130° C. for 45 minutes. The mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and water. The aqueous layer was acidified with hydrochloric acid (1M) and extracted with ethyl acetate, washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 6-(benzenesulphonylmethyl)-2-(2-t-butoxyaminoethoxy)-3-ethylbenzoic acid (0.075 g) as a colourless gum.

Aufarbeitung

customThe mixture was evaporated to dryness
customthe residue was partitioned between ethyl acetate and water
extractionextracted with ethyl acetate
washwashed with water
dry with materialdried (Na2SO4)
filtrationfiltered
customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-77143d829f634b9ba09837eb26f440eb
Quelldatensatz: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09067905B2

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