Sodium Iodide → (2-Benzyloxycarbonylamino-ethyl)-phosphonic acid monoethyl ester

HRID 1886998Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:8])[O:5]CC)[CH3:2].[Na+].[I-]>N1C=CC=CC=1>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:5])[OH:8])[CH3:2]

Participants

Conditions

Temperature: 115 °C

Procedure

(2-Benzyloxycarbonylamino-ethyl)-phosphonic acid diethyl ester (5.77 g, 18.3 mmol) was dissolved in pyridine (61 mL). To this solution was added NaI (13.7 g, 92 mmol). The mixture was heated at 115° C. overnight. The next day the reaction was determined, by LC/MS, to be largely complete. The reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in H2O and extracted with Et2O. The water was then cooled in an ice bath and the adjusted to pH 2 with 2N HCl. The water was then extracted with CH2Cl2 and the combined organic layers were washed with brine and dried over Na2SO4. The drying agent was removed by vacuum filtration and the filtrate was concentrated to yield (2-benzyloxycarbonylamino-ethyl)-phosphonic acid monoethyl ester (4.68 g, 89%) as an oil that turned to a waxy solid under high vacuum.

Workup

temperatureThe reaction was cooled to room temperature
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in H2O
extractionextracted with Et2O
temperatureThe water was then cooled in an ice bath
extractionThe water was then extracted with CH2Cl2
washthe combined organic layers were washed with brine
dry with materialdried over Na2SO4
customThe drying agent was removed by vacuum filtration
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-d261b7406f6c4fe09e889539eb9ef12c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501714B2

Reaction notes

Loading…