Lawesson's reagent → HCID 90192623, compound

HRID 923514Notes

Reaction equation

HRID 923514 reaction equation
[C:1]([NH:4][NH:5][C:6]([C@:8]1([CH3:22])[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[N:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O)(=O)[CH3:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:32]2)=CC=1>C1(C)C=CC=CC=1>[CH3:13][C:10]1([CH3:14])[N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@:8]([CH3:22])([C:6]2[S:32][C:1]([CH3:2])=[N:4][N:5]=2)[CH2:12][O:11]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 90192609HCID 90192609, compound

Product 1

HCID 90192623HCID 90192623, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3.36 g of tert-butyl (4S)-4-[(2-acetylhydrazino)carbonyl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate in 100 ml of toluene was added 2.8 g of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, followed by stirring at 110° C. for 4 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 2.39 g of tert-butyl (4S)-2,2,4-trimethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3-oxazolidine-3-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8802d5a151714894bdfa8c71bda126b9
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

Loading…