Lawesson's reagent → (2S,4R)-4-methanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic acid methyl ester

HRID 1697722Notes

Reaction equation

HRID 1697722 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:7][N:6]1[C:14](=O)[CH2:15][C:16](=[O:18])[CH3:17])=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:7][N:6]1[C:14](=[S:29])[CH2:15][C:16](=[O:18])[CH3:17])=[O:4]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 86646865(2S,4R)-4-Methanesulfonyl-1-(3-oxo-butyryl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 86646866(2S,4R)-4-methanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic acid methyl ester

Procedure

In analogy to the procedure described in example 192 g, (2S,4R)-4-methanesulfonyl-1-(3-oxo-butyryl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with Lawesson's reagent to give the title compound as brown solid. MS (ESI): m/z=308.4 [M+H]+.

Sources & evidence

ORD record
ord-b2d89430cf1d4fd2ad7bb4fa895261d0
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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