Lawesson's reagent → (2S,4R)-1-(2-isobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

HRID 1697614Notes

Reaction equation

HRID 1697614 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.CC1C=CC(S(O)(=O)=O)=CC=1.CC(C)CNN.[CH3:106][O:107][C:108]([C@H:110]1[CH2:114][C@@H:113]([S:115]([C:118]2[CH:123]=[CH:122][CH:121]=[CH:120][C:119]=2[C:124]([F:127])([F:126])[F:125])(=[O:117])=[O:116])[CH2:112][N:111]1[C:128]1[N:129]([CH2:134][CH:135]([CH3:137])[CH3:136])[N:130]=[C:131]([CH3:133])[CH:132]=1)=[O:109]>>[CH3:106][O:107][C:108]([C@@H:110]1[CH2:114][C@@H:113]([S:115]([C:118]2[CH:123]=[CH:122][CH:121]=[CH:120][C:119]=2[C:124]([F:127])([F:125])[F:126])(=[O:117])=[O:116])[CH2:112][N:111]1[C:128]1[N:129]([CH2:134][CH:135]([CH3:137])[CH3:136])[N:130]=[C:131]([CH3:133])[CH:132]=1)=[O:109]

Participants

6

Reactant 5

HCID 87949Lawesson's reagentHCID 12644265(2-Methylpropyl)-hydrazine 4-methylbenzenesulfonateHCID 59543690(2S,4R)-1-(5-Methyl-2-phenyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid (1-cyano-cyclopropyl)-amideHCID 66770942(2R,4R)-1-(2-isobutyl-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 66770783(2S,4R)-1-(2-isobutyl-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 (2-methylpropyl)-hydrazine 4-methylbenzenesulfonate (CAS Reg. No. 112306-59-9) to give a mixture of the title compound and (2R,4R)-1-(2-isobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as yellow solid. MS (ESI): m/z=474.2 [M+H]+.

Workup

  1. custom112306-59-9) to give

Sources & evidence

ORD record
ord-52648e2a2f734bfda84205c34f658b45
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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