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

HRID 1819300ノート

反応式

HRID 1819300 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-23517ca20640462884b5771a90f574d5
出典データセット
uspto-grants-2009_10
特許番号
US07601728B2

反応ノート

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