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

HRID 1697667Notes

Reaction equation

HRID 1697667 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](=[O:32])[CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=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:43])[CH2:24][C:25](=[O:32])[CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:4]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 86646856(2S,4R)-1-[3-oxo-3-(tetrahydro-pyran-4-yl)-propionyl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 86646857(2S,4R)-1-[3-oxo-3-(tetrahydro-pyran-4-yl)-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-oxo-3-(tetrahydro-pyran-4-yl)-propionyl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with Lawesson's reagent to give the title compound as yellow oil. MS (ESI): m/z=508.1 [M+H]+.

Sources & evidence

ORD record
ord-928690f60066489ebde6e331dd05589f
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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