Lawesson's reagent → HCID 54281150, compound

HRID 927442Notes

Reaction equation

HRID 927442 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

HCID 87949Lawesson's reagentHCID 7201299N~2~-(tert-Butoxycarbonyl)-L-leucinamide

Product 1

HCID 54281150HCID 54281150, compoundYield 140%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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]+.

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel, 30 g, ethyl acetate/MeOH, 20/1)

Sources & evidence

ORD record
ord-ee30f376292d4e7b8d7737ccddfe3824
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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