HCID 11759759, compound → HCID 89630158, compound

HRID 578610Notes

Reaction equation

HRID 578610 reaction equation
[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]

Participants

7

Reactant 3

HCID 11759759HCID 11759759, compoundHCID 15153821HCID 15153821, compoundHCID 178418250HCID 178418250, compound

Product 1

HCID 89630158HCID 89630158, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-31090dd04dc34820b2964d556adf61e7
Source dataset
uspto-grants-2015_05
Patent number
US09040602B2

Reaction notes

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