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

HRID 736721ノート

反応式

HRID 736721 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-97f0c2e7b95843e7a3130614d0f3210d
出典データセット
uspto-grants-2009_09
特許番号
US07595327B2

反応ノート

読み込み中…