Iodopropargyl alcohol → N-iodopropargyloxycarbonyl glycine iodopropargyl ester

HRID 248314Notes

Reaction equation

[I:1][N:2]([C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[I:13][CH:14](O)[C:15]#[CH:16].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl.O1CCOCC1.CN(C)C1C=CN=CC=1>[I:13][CH:14]([O:5][C:4](=[O:6])[CH2:3][N:2]([C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[I:1])[C:15]#[CH:16]

Participants

Conditions

Temperature: 0 °C

Procedure

N-Iodopropargyloxycarbonyl glycine (compound 1, 4.96 g., 17.52 mmole) was dissolved in a mixture of methylene chloride and 1,4-dioxane (450 ml., 20 ml. respectively) and cooled to 0° C. with an ice bath. Iodopropargyl alcohol (3.51 g., 19.29 mmole) was added, followed by 4-dimethylaminopyridine (0.22 g., 1.80 mmole) and N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (4.17 g., 21.75 mmole). The reaction mixture was stirred at 4° C. for 17 hours. Upon warming to room temperature, the reaction mixture was diluted with methylene chloride, washed with water, 10% aqueous potassium hydrogen sulfate, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford N-iodopropargyloxycarbonyl glycine iodopropargyl ester (compound 4) as a white crystalline solid (8.26 g.). m.p. 86°-88° C.; 1H-NMR (200 MHz, CDCl3) δppm =4.05, d, J=5.6 Hz., 2H (NH--CH2 --), 4.89, d, J=10.2 Hz., 4H (C--CH2 --O), 5.32, m, 1H (--NH--).

Workup

temperatureUpon warming to room temperature
washwashed with water, 10% aqueous potassium hydrogen sulfate, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-186f3ef1fa4a45fbbd305e7c3ccf33ad
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05209930

Reaction notes

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