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HCID 11759759、化合物 → HCID 89630158、化合物

HRID 578610
ノート
印刷プレビュー

反応式

HRID 578610 の反応式
[O:1]([C:3]#[N:4])[K].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:21])[C:18]([CH3:20])=[CH2:19].[CH2:22]([O:24][P:25]([CH2:30][CH:31]([CH2:41][OH:42])[CH2:32][P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])(=[O:29])[O:26][CH2:27][CH3:28])[CH3:23]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C(#N)C.ClCCl>[CH2:35]([O:34][P:33]([CH2:32][CH:31]([CH2:41][O:42][C:3](=[O:1])[NH:4][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:21])[C:18]([CH3:20])=[CH2:19])[CH2:30][P:25](=[O:29])([O:26][CH2:27][CH3:28])[O:24][CH2:22][CH3:23])(=[O:40])[O:37][CH2:38][CH3:39])[CH3:36]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11759759HCID 11759759、化合物HCID 15153821HCID 15153821、化合物HCID 178418250HCID 178418250、化合物

生成物 1

HCID 89630158HCID 89630158、化合物収率 90%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 6342Acetonitrile
溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

KOCN (3.33 g, 41.0 mmol, 5.85 eq.) and Bu4NBr (1.77 g, 5.49 mmol, 0.8 eq.) were added to a solution of the 10-bromodecylmethacrylate from the 1st step (8.36 g, 27.4 mmol, 3.9 eq.) in anhydrous acetonitrile (55 ml) and the reaction mixture was stirred for 64 h. The reaction mixture was subsequently concentrated in vacuo and hexane (100 ml) was added. After filtration of the obtained solution and concentrating in vacuo 4.75 g of a yellow oil was obtained. To this oil a solution of 2-hydroxymethyl-1,3-propylene-bisphosphonic acid tetraethylester (2.41 g, 7.0 mmol) in anhydrous dichloromethane (2.0 ml) and a 1% solution of Metatin 712 in dichloromethane (2.0 ml) were added and the reaction mixture was stirred for 15 h at room temperature. After concentrating in vacuo the obtained crude product was purified by column chromatography (eluent: ethyl acetate/methanol 95:5). 3.85 g (90% yield) of the product was obtained as a colorless oil.

後処理

  1. concentrationThe reaction mixture was subsequently concentrated in vacuo and hexane (100 ml)
  2. additionwas added
  3. filtrationAfter filtration of the obtained solution
  4. concentrationconcentrating in vacuo 4.75 g of a yellow oil
  5. customwas obtained
  6. stirringthe reaction mixture was stirred for 15 h at room temperature
  7. concentrationAfter concentrating in vacuo the
  8. customobtained crude product
  9. customwas purified by column chromatography (eluent: ethyl acetate/methanol 95:5)

出典と根拠

ORDレコード
ord-31090dd04dc34820b2964d556adf61e7
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040602B2

反応ノート

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