Lawesson's reagent → (2S,4R)-1-(2-Benzyl-5-methyl-2H-pyrazol-3-yl)-4-(2-chloro-4-fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697652Notes

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][C:16]([F:19])=[CH:15][C:14]=2[Cl:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:21](=O)[CH2:22][C:23](=O)[CH3:24])=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.Cl.Cl.[CH2:51]([NH:58][NH2:59])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=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][C:16]([F:19])=[CH:15][C:14]=2[Cl:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:21]1[N:58]([CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[N:59]=[C:23]([CH3:24])[CH:22]=1)=[O:4]

Participants

Reactant 3

HCID 87949Lawesson's reagent

HCID 146540Benzylhydrazine dihydrochloride

HCID 86646855(2S,4R)-methyl 4-(2-chloro-4-fluorophenylsulfonyl)-1-(3-oxobutanoyl)pyrrolidine-2-carboxylate

Product 1

HCID 66770518(2S,4R)-1-(2-Benzyl-5-methyl-2H-pyrazol-3-yl)-4-(2-chloro-4-fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 192 h, (2S,4R)-4-(2-chloro-4-fluoro-benzenesulfonyl)-1-(3-oxo-butyryl)-pyrrolidine-2-carboxylic acid methyl ester (example 375b) was reacted with Lawesson's reagent (CAS Reg. No. 19172-47-5) and benzylhydrazine dihydrochloride (CAS Reg. No. 20570-96-1) to give the title compound as yellow oil. MS (ESI): m/z=492.3 [M+H]+.

Sources & evidence

ORD record: ord-85847e83a3bd454d9c393d47a7c6b2e5
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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