Lawesson's reagent → (S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1,3,4-thiadiazol-2-yl)pyrrolidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Lawesson's reagent	HCID 87949	—
Reactant	(S)-t-Butyl 2-(2-(2-(3,4-dimethoxyphenoxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate	HCID 86706750	—
Solvent	Toluene	HCID 1140	—
Product	(S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1,3,4-thiadiazol-2-yl)pyrrolidine-1-carboxylate	HCID 86706771	54.1%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a toluene (30 ml) solution of the compound (540 mg) obtained in Example 8-(1), Lawesson's reagent (750 mg) was added and the mixture was stirred at 90° C. for 6 hours. After adding water, extraction was conducted with AcOEt. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (291 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181229B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-d87a05b49c254b14b001469273645b3a
Source note	uspto-grants-2015_11