Reaktion #91494

Reaktionsgleichung

iodomethane

compound 68a

tert-Butyl 4-(4-(3,4,5-trimethoxybenzoyl)thiazol-2-yl)benzylcarbamate

sodium hydride

→

compound 71a

Ausbeute 61.3%

tert-Butyl methyl(4-(4-(3,4,5-trimethoxybenzoyl)thiazol-2-yl)benzyl)carbamate

Ausbeute 61.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was quenched with a sat. NaHCO3 solution
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   Trocknendried with MgSO4
4. 4
   SonstigeThe solvent was removed under reduced pressure
5. 5
   Sonstigeto yield a crude product, which
6. 6
   Sonstigewas purified by column chromatography

Vorschrift

At 0° C., to a solution of compound 68a (100 mg, 0.2 mmol) in 5 mL DMF was added sodium hydride (10 mg, 0.2 mmol), then iodomethane (77 mg, 0.4 mmol) was added to the reaction mixture and stirred at RT overnight. The mixture was quenched with a sat. NaHCO3 solution, extracted with ethyl acetate and dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound 71a. Yield: 61.3%. 1H NMR (500 MHz, DMSO-d6) δ 8.30 (s, 1H), 8.02 (d, 2H, J=8.0 Hz), 7.82 (s, 2H), 7.36 (br, 2H), 4.50 (s, 2H), 4.00 (s, 3H), 3.98 (s, 6H), 2.90 (d, br, 3H), 1.50 (s, 9H). MS (ESI) m/z 521.2 (M+Na)+, 496.9 (M−H)−.

Quelle