Triethylamine → HCID 89614204, compound

HRID 578611Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:9])[C:5]([CH2:7]Cl)=[CH2:6])[CH3:2].[CH2:10]([O:12][P:13]([CH2:18][CH:19]([CH2:29][OH:30])[CH2:20][P:21](=[O:28])([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])(=[O:17])[O:14][CH2:15][CH3:16])[CH3:11].C(N(CC)CC)C>C1COCC1>[CH2:23]([O:22][P:21]([CH2:20][CH:19]([CH2:29][O:30][CH2:7][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:9])=[CH2:6])[CH2:18][P:13](=[O:17])([O:14][CH2:15][CH3:16])[O:12][CH2:10][CH3:11])(=[O:28])[O:25][CH2:26][CH3:27])[CH3:24]

Participants

Conditions

Temperature: 70 °C

Procedure

Ethyl-2-(chloromethyl)-acrylate (3.86 g, 26.0 mmol, 1.5 eq.) was added to a solution of 2-hydroxymethyl-1,3-propylene-bisphosphonic acid tetraethylester (6.0 g, 17.3 mmol) and triethylamine (3.62 ml, 26 mmol, 1.5 eq.) in anhydrous THF (30 ml), and the reaction mixture was stirred for 45 h at 70° C. After concentrating in vacuo deionized water (50 ml) was added and the obtained solution was extracted with ethylacetate (3×50 ml). The combined organic phases were dried with anhydrous sodium sulphate. After removal of the solvent under reduced pressure the obtained crude product was purified by column chromatography (eluent: ethylacetate/methanol 98:2). 3.77 g (48% yield) of the product was obtained as a yellowish oil.

Workup

concentrationAfter concentrating in vacuo deionized water (50 ml)
additionwas added
extractionthe obtained solution was extracted with ethylacetate (3×50 ml)
dry with materialThe combined organic phases were dried with anhydrous sodium sulphate
customAfter removal of the solvent under reduced pressure the
customobtained crude product
customwas purified by column chromatography (eluent: ethylacetate/methanol 98:2)

Sources & evidence

ORD record: ord-84f9ab5e258a4a0c97e0075199b343f1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040602B2

Reaction notes

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