Lawesson's reagent → (S)-tert-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)thiazol-2-yl)pyrrolidine-1-carboxylate

HRID 710067Notes

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](=O)[CH2:9][NH:10][C:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=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:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:10][CH:9]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a toluene (5 ml) solution of the compound (0.287 g) obtained in Example 19-(4), Lawesson's reagent (0.275 g) was added and the mixture was stirred at 110° C. for an hour. After reversion to room temperature, the reaction mixture was concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (0.100 g, colorless amorphous.)

Workup

concentrationAfter reversion to room temperature, the reaction mixture was concentrated
customto give a crude product, which
customwas further purified by silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record: ord-baab8d47f0be4c438ed7557446e782a1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181229B2

Reaction notes

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