Methyl Acrylate → HCID 14134435, compound

HRID 1885135Notes

Reaction equation

[CH3:1][O:2][P:3]([CH:5]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH3:6])[OH:4].C[O-].[Na+].[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23]>CO.Cl>[CH3:1][O:2][P:3]([CH:5]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])[CH3:6])([CH2:23][CH2:22][C:21]([O:25][CH3:26])=[O:24])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 0.36 gm (0.0014 mol) of 1-benzyloxycarbonylaminoethylphosphonous acid methyl ester in 3 ml of methanol at 0° C. was added a solution of sodium methoxide in methanol (0.77 ml of a 2N solution) dropwise over 10 minutes whereupon was then added methyl acrylate 0.126 ml (0.0014 mol). The reaction mixture was stirred 30 minutes at 0° C. and 4 hours at room temperature whereupon it was diluted with 1N HCl. The mixture was extracted twice with ethyl acetate. The organic fractions were dried over sodium sulfate, filtered through magnesium sulfate and evaporated in vacuo. The product mixture was purified by chromatography (silica, 9:1, ethylacetate:acetonitrile) to give 0.34 gm of methyl-1-benzyloxycarbonylaminoethyl-[2-carbomethoxy-1-ethyl]phosphinate.

Workup

extractionThe mixture was extracted twice with ethyl acetate
dry with materialThe organic fractions were dried over sodium sulfate
filtrationfiltered through magnesium sulfate
customevaporated in vacuo
customThe product mixture was purified by chromatography (silica, 9:1, ethylacetate:acetonitrile)

Sources & evidence

ORD record: ord-0b96062fc16e4aa5a72fd8546df2fcb4
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05143908

Reaction notes

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