Diisopropylethylamine → Di-tert-butyl cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-1,3-dicarboxylate

HRID 736721Notes

Reaction equation

HRID 736721 reaction equation
[NH2:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][C@H:3]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CCN(C(C)C)C(C)C.Cl.[CH3:31][C:32]1[CH:41]=[C:40]([CH2:42][O:43][C:44]2[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:46][CH:45]=2)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1>CN(C)C=O>[CH3:31][C:32]1[CH:41]=[C:40]([CH2:42][O:43][C:44]2[CH:49]=[CH:48][C:47]([S:50]([NH:1][C@H:2]3[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][C@H:3]3[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])(=[O:52])=[O:51])=[CH:46][CH:45]=2)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11483050(3R,4R)-di-tert-butyl 4-aminopyrrolidine-1,3-dicarboxylateHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

Product 1

HCID 68818597Di-tert-butyl cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-1,3-dicarboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the stirred solution of 687 mg (2.4 mol) of di-tert-butyl cis-4-aminopyrrolidine-1,3-dicarboxylate (prepared according to J. Med. Chem. 2001, 44, 1192-1201) was added 2.1 mL of Hunig's base in 10 mL of N,N-dimethylformamide and 922 mg of 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride. The solution was stirred at room temperature overnight. The N,N-dimethylformamide was removed in vacuo, and the residue was dissolved in 100 mL of chloroform. The chloroform solution was washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified using flash chromatography on silica gel eluting with ethyl acetate/hexane to provide 929 mg (65% yield) of di-tert-butyl cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-1,3-dicarboxylate. MS: 598.4 (M+H)+

Workup

  1. customThe N,N-dimethylformamide was removed in vacuo
  2. dissolutionthe residue was dissolved in 100 mL of chloroform
  3. washThe chloroform solution was washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified

Sources & evidence

ORD record
ord-97f0c2e7b95843e7a3130614d0f3210d
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

Loading…