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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(tert-Butoxycarbonyl-{4-[tert-butoxycarbonyl-(2-octadec-8-enyloxycarbonyl-ethyl)-amino]-butyl}-amino)-propionic acid octadec-8-enyl ester

HRID 31537
ノート
印刷プレビュー

反応式

HRID 31537 の反応式
[C:1]([CH2:6][CH2:7][N:8]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O:3][CH2:4][CH3:5])=[O:2].CN([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40]N=1)C.C(O)C[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]/[CH:52]=[CH:53]\[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61].CCN=C=N[CH2:68][CH2:69][CH2:70]N(C)C>ClCCl>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][CH2:21][N:13]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][N:8]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:7][CH2:6][C:1]([O:3][CH2:4][CH2:5][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH:56]=[CH:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH3:46])=[O:2])[CH2:27][CH2:38][CH2:43][CH2:42][CH2:41][CH2:40][CH:46]=[CH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:70][CH2:69][CH3:68]
参加物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 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 5284499Oleyl AlcoholHCID 86618851N,N'-Bis-(2-carbethoxyethyl)-N,N'-bis-(tert-butoxycarbonyl)-1,4-diaminobutane

生成物 1

HCID 866188503-(tert-Butoxycarbonyl-{4-[tert-butoxycarbonyl-(2-octadec-8-enyloxycarbonyl-ethyl)-amino]-butyl}-amino)-propionic acid octadec-8-enyl ester
収率 99.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of the N-protected amino acid 4 (n=4; 15.2 g, 35.1 mmol), dimethylaminopyridine (1.70 g, 14.0 mmol) and oleyl alcohol (18.4 g, 68.4 mmol) in dichloromethane (200 mL) was added a solution of EDCI (13.1 g, 68.4 mmol), in dichloromethane (50 mL) at 0° C. The resulting mixture was allowed to warm to room temperature and then stirred under N2 for 18 h. Dichloromethane (250 mL) was added and the mixture was washed with brine (4×200 mL), dried (Na2SO4) and concentrated in vacuo to leave an oil which was purified by column chromatography eluting with a solvent gradient of CH2Cl2 (50-90%) in hexane to afford the ester 5 as a colourless oil (13.0 g, 40%).

後処理

  1. customat 0° C
  2. washthe mixture was washed with brine (4×200 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto leave an oil which
  6. customwas purified by column chromatography
  7. washeluting with a solvent gradient of CH2Cl2 (50-90%) in hexane

出典と根拠

ORDレコード
ord-4f0683b1699744fda12b8eda8e175f72
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07425645B2

反応ノート

読み込み中…

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