Lawesson's reagent → (2S,4R)-1-(3-Cyclopropyl-3-oxo-thiopropionyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697676Notes

Reaction equation

HRID 1697676 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:23](=O)[CH2:24][C:25]([CH:27]1[CH2:29][CH2:28]1)=[O:26])=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:23](=[S:40])[CH2:24][C:25]([CH:27]1[CH2:29][CH2:28]1)=[O:26])=[O:4]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 86646850(2S,4R)-1-(3-Cyclopropyl-3-oxo-propionyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 86646858(2S,4R)-1-(3-Cyclopropyl-3-oxo-thiopropionyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 192f, (2S,4R)-1-(3-cyclopropyl-3-oxo-propionyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (example 363a) was reacted with Lawesson's reagent to give the title compound as brown oil. MS (ESI): m/z=364.1 [M+H]

Sources & evidence

ORD record
ord-8f312cbcd49f42a7be721e09d2a62c83
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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