Trifluoroacetic acid → (2S,4R)-4-[4-(2,2,2-Trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697595Notes

Reaction equation

HRID 1697595 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]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:15][C:14]=2[C:25]([F:28])([F:27])[F:26])(=[O:12])=[O:11])[CH2:7][N:6]1C(OC(C)(C)C)=O)=[O:4].COC([C@@H]1C[C@@H](S(C2C=CC(F)=CC=2C(F)(F)F)(=O)=O)CN1C(OC(C)(C)C)=O)=O.FC(F)(F)C(O)=O.COC([C@@H]1C[C@@H](S(C2C=CC(F)=CC=2C(F)(F)F)(=O)=O)CN1)=O>ClCCl>[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]([O:19][CH2:20][C:21]([F:22])([F:23])[F:24])=[CH:15][C:14]=2[C:25]([F:27])([F:26])[F:28])(=[O:12])=[O:11])[CH2:7][NH:6]1)=[O:4]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 66770389HCID 66770389, compoundHCID 66771094(2S,4R)-1-tert-butyl 2-methyl 4-(4-fluoro-2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-1,2-dicarboxylateHCID 86646837(2S,4R)-1-tert-Butyl 2-methyl 4-(4-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 86646838(2S,4R)-4-[4-(2,2,2-Trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-2-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 253a, (2S,4R)-4-[4-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester containing (2S,4R)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester was treated with trifluoroacetic acid in dichloromethane to give a mixture of the title compound and (2S,4R)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as yellow oil. MS (ESI): m/z=436.2 [M+H]+.

Workup

  1. customto give

Sources & evidence

ORD record
ord-f3665c4db2514743a06b140bf05669e7
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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