Lawesson's reagent → (2S,4R)-Methyl 4-(2-chloro-4-fluorophenylsulfonyl)-1-(3-oxobutanethioyl)pyrrolidine-2-carboxylate

HRID 1697740Notes

Reaction equation

HRID 1697740 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([C@H:12]1[CH2:16][N:15]([C:17](=O)[CH2:18][C:19](=[O:21])[CH3:20])[C@H:14]([C:23]([O:25][CH3:26])=[O:24])[CH2:13]1)(=[O:11])=[O:10].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([C@H:12]1[CH2:16][N:15]([C:17](=[S:36])[CH2:18][C:19](=[O:21])[CH3:20])[C@H:14]([C:23]([O:25][CH3:26])=[O:24])[CH2:13]1)(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 86646855(2S,4R)-methyl 4-(2-chloro-4-fluorophenylsulfonyl)-1-(3-oxobutanoyl)pyrrolidine-2-carboxylate

Product 1

HCID 86646870(2S,4R)-Methyl 4-(2-chloro-4-fluorophenylsulfonyl)-1-(3-oxobutanethioyl)pyrrolidine-2-carboxylate

Procedure

In analogy to the procedure described in example 192 g, (2S,4R)-methyl 4-(2-chloro-4-fluorophenylsulfonyl)-1-(3-oxobutanoyl)pyrrolidine-2-carboxylate (example 375b) was reacted with Lawesson's reagent (CAS Reg. No. 19172-47-5) to give the title compound as orange foam. MS (ESI): m/z=421.9 [M+H]+.

Sources & evidence

ORD record
ord-319b8940e86d49c6abd50edc7a54e6e5
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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