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

HRID 1697600Notes

Reaction equation

HRID 1697600 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)CCCCC1.[CH3:98][O:99][C:100]([C@H:102]1[CH2:106][C@@H:105]([S:107]([C:110]2[CH:115]=[CH:114][CH:113]=[CH:112][C:111]=2[C:116]([F:119])([F:118])[F:117])(=[O:109])=[O:108])[CH2:104][N:103]1[C:120]1[N:121]([CH:126]2[CH2:131][CH2:130][CH2:129][CH2:128][CH2:127]2)[N:122]=[C:123]([CH3:125])[CH:124]=1)=[O:101]>>[CH3:98][O:99][C:100]([C@@H:102]1[CH2:106][C@@H:105]([S:107]([C:110]2[CH:115]=[CH:114][CH:113]=[CH:112][C:111]=2[C:116]([F:119])([F:117])[F:118])(=[O:109])=[O:108])[CH2:104][N:103]1[C:120]1[N:121]([CH:126]2[CH2:131][CH2:130][CH2:129][CH2:128][CH2:127]2)[N:122]=[C:123]([CH3:125])[CH:124]=1)=[O:101]

Participants

6

Reactant 5

HCID 87949Lawesson's reagentHCID 207836Cyclohexylhydrazine hydrochlorideHCID 59543690(2S,4R)-1-(5-Methyl-2-phenyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid (1-cyano-cyclopropyl)-amideHCID 66770402(2R,4R)-1-(2-cyclohexyl-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 66770516(2S,4R)-1-(2-Cyclohexyl-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 cyclohexylhydrazine hydrochloride (CAS Reg. No. 24214-73-1) to give a mixture of the title compound and (2R,4R)-1-(2-cyclohexyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as brown oil. MS (ESI): m/z=500.3 [M+H]+.

Workup

  1. custom24214-73-1) to give

Sources & evidence

ORD record
ord-04292a36a41848a7a9f8c89bcf6e2623
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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