Water → N-(1-{(3R)-3-[(tert-Butoxycarbonyl)amino]-piperidin-1-yl}-2,2-dicyanovinyl)-N-(2-chlorobenzyl)glycine ethyl ester

HRID 1819300노트

반응식

HRID 1819300 반응식
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][NH:6][C:7]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14]1)=[C:8]([C:11]#[N:12])[C:9]#[N:10])[CH3:2].[Cl:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31]Br.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]([C:7]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14]1)=[C:8]([C:9]#[N:10])[C:11]#[N:12])[CH2:31][C:30]1[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=1[Cl:28])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 86625681N-(1-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-2,2-dicyanovinyl)glycine ethyl ester

생성물 1

HCID 86625680N-(1-{(3R)-3-[(tert-Butoxycarbonyl)amino]-piperidin-1-yl}-2,2-dicyanovinyl)-N-(2-chlorobenzyl)glycine ethyl ester

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of N-(1-{(3R)-3-[(tertbutoxycarbonyl)amino]piperidin-1-yl}-2,2-dicyanovinyl)glycine ethyl ester (300 mg), 2-chlorobenzyl bromide (0.15 ml) and potassium carbonate (330 mg) in acetone (4 ml) was stirred at 25° C. for 24 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution, dried over sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1) to obtain the title compound (340 mg) as a white amorphous substance.

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with an aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1)

출처 및 근거

ORD 기록
ord-23517ca20640462884b5771a90f574d5
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601728B2

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