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

HRID 710049노트

반응식

HRID 710049 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c6ddbeae3619443382fac0b2f0710606
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181229B2

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