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Diethylaminoethyl chloride → N-[3,5-bis(decyloxy)phenyl]-N-[2-[2-(diethylamino)ethoxy]-2-oxoethyl]glycine 2-(diethylamino)ethyl ester dihydrochloride

HRID 1757861
ノート
印刷プレビュー

反応式

HRID 1757861 の反応式
[C:1]([CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:13]=[C:12]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2].[CH2:38]([N:40]([CH2:44][CH3:45])[CH2:41][CH2:42][Cl:43])[CH3:39].[CH:46]([N:49]([CH2:53][CH3:54])[CH:50](C)[CH3:51])(C)[CH3:47]>CN(C=O)C>[ClH:43].[ClH:43].[CH2:38]([N:40]([CH2:44][CH3:45])[CH2:41][CH2:42][O:2][C:1](=[O:3])[CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:13]=[C:12]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:11]=1)[CH2:6][C:7]([O:9][CH2:47][CH2:46][N:49]([CH2:53][CH3:54])[CH2:50][CH3:51])=[O:8])[CH3:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 13364Diethylaminoethyl chlorideHCID 81531DiisopropylethylamineHCID 192621N-(carboxymethyl)-N-(3,5-bis(decyloxy)-phenyl)glycine

生成物 1

HCID 67788036N-[3,5-bis(decyloxy)phenyl]-N-[2-[2-(diethylamino)ethoxy]-2-oxoethyl]glycine 2-(diethylamino)ethyl ester dihydrochloride収率 36.8%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A mixture of 0.50 g (0.96 mmol) of N-(carboxymethyl)-N-[3,5-bis(decyloxy)phenyl]glycine, 1.3 g (9.6 mmol) of 2-diethylaminoethyl chloride and 1.34 ml (7.7 mmol) of N,N-diisopropyl ethylamine in 15 ml of DMF was stirred at room temperature for 48 hours. The reaction mixture was concentrated on the oil pump and the residue was treated with NaHCO3 solution. The product was extracted with ethyl acetate and the dried extract was concentrated at reduced pressure to an oil which was purified by chromatography on 25 g of 230-400 mesh silica gel using methylene chloride(90):methanol(10):concentrated ammonium hydroxide(0.1). The resultant pure free base (0.51 g) was convened to the dihydrochloride salt by treatment of a methylene chloride solution with 0.95 ml of 3N HCl in ethanol. After concentration, the product was dissolved in ether and stored at -18° until crystals formed. Filtration gave 0.28 g, mp 132°-135° of N-[3,5-bis(decyloxy)phenyl]-N-[ 2-[2-(diethylamino)ethoxy]-2-oxoethyl]glycine 2-(diethylamino)ethyl ester dihydrochloride.

後処理

  1. concentrationThe reaction mixture was concentrated on the oil pump
  2. additionthe residue was treated with NaHCO3 solution
  3. extractionThe product was extracted with ethyl acetate
  4. extractionthe dried extract
  5. concentrationwas concentrated at reduced pressure to an oil which
  6. customwas purified by chromatography on 25 g of 230-400 mesh silica gel
  7. concentrationAfter concentration
  8. dissolutionthe product was dissolved in ether
  9. customstored at -18° until crystals
  10. customformed
  11. filtrationFiltration

出典と根拠

ORDレコード
ord-9e79b446b8f2450baafd57c363b90a13
出典データセット
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05446189

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート