Lawesson's reagent → Boc-l-leucine thioamide
Reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH:5]([CH3:7])[CH3:6].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[C:11]([O:10][C:9](=[O:15])[NH:8][C@H:3]([C:2](=[S:26])[NH2:1])[CH2:4][CH:5]([CH3:7])[CH3:6])([CH3:14])([CH3:13])[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of (S)-tert-butyl 1-amino-4-methyl-1-oxopentan-2-ylcarbamate (1.8 g, 8 mmol) and Lawesson's reagent (1.58 g, 4 mmol) in toluene (20 mL) was stirred at 90° C. for 2.5 h. After removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel, 30 g, ethyl acetate/MeOH, 20/1) to yield the title compound (1.38 g, 72%) as yellow solid; MS: m/e 269.2 [M+H]+.