Trifluoroacetic acid → cis-4-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-3-carboxylic acid

HRID 736732Notes

Reaction equation

HRID 736732 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][C@H:24]3[CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][C@H:25]3[C:36]([O:38]C(C)(C)C)=[O:37])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][C@H:24]3[CH2:28][NH:27][CH2:26][C@H:25]3[C:36]([OH:38])=[O:37])(=[O:21])=[O:22])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68818597Di-tert-butyl cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-1,3-dicarboxylate

Product 1

HCID 68817812cis-4-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the stirred solution of 299 mg of di-tert-butyl cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-1,3-dicarboxylate (Example 17, Step 1) in 4 mL of dichloromethane was slowly added 3 mL of trifluoroacetic acid. The solution was stirred at room temperature for 3 hr. After removal of the volatile material, cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-3-carboxylic acid was obtained in quantitative yield without further purification. MS: 442.3 (M+H)+

Workup

  1. customAfter removal of the volatile material

Sources & evidence

ORD record
ord-44639a4b5abf4965abb412d513d1cb2c
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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