Water → HCID 11999020, Verbindung

HRID 1948450Notizen

Reaktionsgleichung

[CH2:1]([NH:4][S:5]([C:8]1[S:12][C:11](Br)=[C:10]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[CH3:23])[CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].C([Li])CCC.O>C1COCC1>[CH2:1]([NH:4][S:5]([C:8]1[S:12][CH:11]=[C:10]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[CH3:23])[CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3]

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

N-(5-{5-[(allylamino)sulfonyl]-2-bromo-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide obtained in Step I as described above (35 mg; 0.08 mmol; 1 eq), is dissolved in dry THF (5 ml) at −70° C. under an inert atmosphere. n-Butyllithium (0.18 ml; 1 M; 0.18 mmol; 2.20 eq) is added slowly and reaction stirred at −70° C. for 1 hour before being hydrolyzed with water (0.3 ml). Reaction is warmed up to room temperature before being concentrated to dryness. Residue is taken up with water (2 ml) and EtOAc (10 ml). The organic phases are decanted, dried over MgSO4, filtrated and evaporated. Title compound is purified by reverse preparative HPLC, affording Compound (49) as a white powder (3 mg; 10%).

Aufarbeitung

customreaction
customReaction
temperatureis warmed up to room temperature
concentrationbefore being concentrated to dryness
customThe organic phases are decanted
dry with materialdried over MgSO4
filtrationfiltrated
customevaporated
customTitle compound is purified by reverse preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-ce9274d6530945c18375dd8a8201c8ab
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08399497B2

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