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

HRID 1697651Notes

Reaction equation

HRID 1697651 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.[CH:50]1([NH:54][NH2:55])[CH2:53][CH2:52][CH2:51]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:11])=[O:12])[CH2:7][N:6]1[C:21]1[N:54]([CH:50]2[CH2:53][CH2:52][CH2:51]2)[N:55]=[C:23]([CH3:24])[CH:22]=1)=[O:4]

Participants

4

Reactant 3

HCID 87949Lawesson's reagentHCID 19432792Cyclobutylhydrazine--hydrogen chloride (1/1)HCID 86646855(2S,4R)-methyl 4-(2-chloro-4-fluorophenylsulfonyl)-1-(3-oxobutanoyl)pyrrolidine-2-carboxylate

Product 1

HCID 67278407(2S,4R)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-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 was reacted with Lawesson's reagent (CAS Reg. No. 19172-47-5) and cyclobutylhydrazine hydrochloride (CAS Reg. No. 158001-21-9) to give the title compound as colorless oil. MS (ESI): m/z=456.2 [M+H]+.

Sources & evidence

ORD record
ord-4f43b368285646759fd187abe1b2975f
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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