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

HRID 710058Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8]([NH:10][NH:11][C:12]([C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=O)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8]1[S:40][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:11][N:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

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).

Workup

additionAfter adding
extractionwater, extraction
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel chromatography (AcOEt/hexane)

Sources & evidence

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

Reaction notes

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