Lawesson's reagent → (2S,4R)-4-Cyclopropylmethanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697715Notes

Reaction equation

HRID 1697715 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17](=O)[CH2:18][C:19](=[O:21])[CH3:20])=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17](=[S:32])[CH2:18][C:19](=[O:21])[CH3:20])=[O:4]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 86646863(2S,4R)-4-cyclopropylmethanesulfonyl-1-(3-oxo-butyryl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 86646864(2S,4R)-4-Cyclopropylmethanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 192 g, (2S,4R)-4-cyclopropylmethanesulfonyl-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=348.4 [M+H]+.

Sources & evidence

ORD record
ord-261e8dc7cb36434abced7eae42703190
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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