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

HRID 1697604Notes

Reaction equation

HRID 1697604 reaction equation
C(C1(NC([C@@H]2C[C@@H](S(C3C=CC=CC=3C(F)(F)F)(=O)=O)CN2C2N(C3C=CC=CC=3)N=C(C)C=2)=O)CC1)#N.COC([C@H]1C[C@@H](S(C2C=CC=CC=2C(F)(F)F)(=O)=O)CN1C(=O)CC(=O)C)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.Cl.C1(NN)CCC1.[CH3:96][O:97][C:98]([C@H:100]1[CH2:104][C@@H:103]([S:105]([C:108]2[CH:113]=[CH:112][CH:111]=[CH:110][C:109]=2[C:114]([F:117])([F:116])[F:115])(=[O:107])=[O:106])[CH2:102][N:101]1[C:118]1[N:119]([CH:124]2[CH2:127][CH2:126][CH2:125]2)[N:120]=[C:121]([CH3:123])[CH:122]=1)=[O:99]>>[CH3:96][O:97][C:98]([C@@H:100]1[CH2:104][C@@H:103]([S:105]([C:108]2[CH:113]=[CH:112][CH:111]=[CH:110][C:109]=2[C:114]([F:117])([F:115])[F:116])(=[O:107])=[O:106])[CH2:102][N:101]1[C:118]1[N:119]([CH:124]2[CH2:127][CH2:126][CH2:125]2)[N:120]=[C:121]([CH3:123])[CH:122]=1)=[O:99]

Participants

6

Reactant 5

HCID 87949Lawesson's reagentHCID 19432792Cyclobutylhydrazine--hydrogen chloride (1/1)HCID 59543690(2S,4R)-1-(5-Methyl-2-phenyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid (1-cyano-cyclopropyl)-amideHCID 66770867(2R,4R)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 86646843(2R,4R)-1-(3-oxo-butyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 66770762(2S,4R)-1-(2-Cyclobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 308d, a mixture of (2S,4R)-1-(3-oxo-butyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (example 192 f) and of (2R,4R)-1-(3-oxo-butyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-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 a mixture of the title compound and (2R,4R)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as white solid. MS (ESI): m/z=472.3 [M+H]+.

Workup

  1. custom158001-21-9) to give

Sources & evidence

ORD record
ord-82706b2bc3064b42aae421d493a4f3ec
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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