Chloroform → (S)-t-Butyl 2-(3-((3,4-dimethoxyphenoxy)methyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylate

HRID 710049ノート

反応式

HRID 710049 の反応式
C(Cl)(Cl)Cl.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[O:10][CH2:11][C:12](=[N:14][OH:15])[NH2:13].[C:21]([O:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C:33](O)=O)=[O:27])([CH3:24])([CH3:23])[CH3:22].CCN=C=NCCCN(C)C.Cl>O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[O:10][CH2:11][C:12]1[N:13]=[C:33]([C@@H:29]2[CH2:30][CH2:31][CH2:32][N:28]2[C:26]([O:25][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:27])[O:15][N:14]=1

参加物

6

反応物 4

HCID 6212ChloroformHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 867067612-(3,4-Dimethoxyphenoxy)-N'-hydroxyacetoimidamide

生成物 1

HCID 86706762(S)-t-Butyl 2-(3-((3,4-dimethoxyphenoxy)methyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylate収率 10.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a CHCl3 (20 ml) solution of the compound (1.0 g) obtained in Example 12-(1) and (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.0 g), WSC.HCl (1.0 g) was added and the mixture was stirred at room temperature for 4 hours. Water was added, followed by extraction with CHCl3. After distilling off the solvent under reduced pressure, the residue was dissolved in toluene (20 ml), followed by refluxing for 2 hours. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (190 mg).

後処理

  1. extractionfollowed by extraction with CHCl3
  2. distillationAfter distilling off the solvent under reduced pressure
  3. dissolutionthe residue was dissolved in toluene (20 ml)
  4. temperatureby refluxing for 2 hours
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-c6ddbeae3619443382fac0b2f0710606
出典データセット
uspto-grants-2015_11
特許番号
US09181229B2

反応ノート

読み込み中…