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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-Methyl-2-(4-{[5-(4-trifluoromethoxy-phenyl)-pent-4-ynoylamino]-methyl}-phenoxy)-propionic acid ethyl ester

HRID 852396
ノート
印刷プレビュー

反応式

HRID 852396 の反応式
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[F:18][C:19]([F:35])([F:34])[O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[C:28][CH2:29][CH2:30][C:31](O)=[O:32])=[CH:23][CH:22]=1.Cl.CN(C)CCCN=C=NCC.OS([O-])(=O)=O.[K+].CCOCC>ClCCl>[CH2:1]([O:3][C:4](=[O:17])[C:5]([CH3:7])([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][NH:16][C:31](=[O:32])[CH2:30][CH2:29][C:28]#[C:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][C:19]([F:34])([F:35])[F:18])=[CH:22][CH:23]=2)=[CH:13][CH:14]=1)[CH3:6])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 161091882-(4-Aminomethyl-phenoxy)-2-methyl-propionic acid ethyl esterHCID 688226854-Pentynoic acid, 5-[4-(trifluoromethoxy)phenyl]-HCID 86584777KHSO4 ether

生成物 1

HCID 694583382-Methyl-2-(4-{[5-(4-trifluoromethoxy-phenyl)-pent-4-ynoylamino]-methyl}-phenoxy)-propionic acid ethyl ester
収率 47.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

0.16 g (0.68 mmol) of 2-(4-aminomethyl-phenoxy)-2-methyl-propionic acid ethyl ester [PCT Int. Appl. WO 2002/096895 A1] and 0.16 g (0.62 mmol) of 5-(4-trifluoromethoxy-phenyl)-pent-4-ynoic acid (example 29D]) were dissolved in 4 ml of dichloromethane. This solution was cooled to 0° C. and then 0.14 g (0.74 mmol) of N-(3-dimethylamino-propyl)-N′-ethyl-carbodiimide-hydrochloride was added and the reaction stirred for 28 hours at ambient temperature. It was subsequently poured into aqueous 10% KHSO4/ether and extracted two fold with ether; the organic layers were washed with aqueous saturated NaHCO3, dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography (SiO2; n-heptane/AcOEt=9:1 to 1:2) to give 0.14 g of the title compound as light brown oil.

後処理

  1. extractionextracted two fold with ether
  2. washthe organic layers were washed with aqueous saturated NaHCO3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (SiO2; n-heptane/AcOEt=9:1 to 1:2)

出典と根拠

ORDレコード
ord-658ee856c0c349c88e9b7b01eb04159b
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07253192B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート