Lawesson's reagent → 5-(Tert-butoxycarbonylamino-methyl)-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester
Reaktionsgleichung
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][NH:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:30][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][N:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To the solution of ethyl 2-(2-(2-(tert-butoxycarbonylamino)acetyl) hydrazinyl)-2-oxoacetate (9-4) (228 mg, 0.6913 mmol) in THF (10 mL) was added lawesson's reagent (354 mg, 0.8669 mmol). The solution was heated to reflux for 3 h. Then solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel with the eluant (PE/EA/NEt3=10/1/1%; 5/1/1%; 2/1/1%). The yellow solid was obtained as the product (520 mg, 69%). 1H NMR (500 MHz, CDCl3) δ 5.31 (br, 1H), 4.76 (d, J=6.1 Hz, 2H), 4.51 (d, J=14, 7.1 Hz, 2H), 1.60-1.39 (m, 12H); LRMS (ESI) calculated M+H for C11H18N3O4S: 288.3; Found: 288.1.