Dicyclohexylcarbodiimide → Diisopropyl ether ethanol

HRID 1939891Notes

Reaction equation

[OH:1][C:2]1[C:10]2N=NNC=2C=C[CH:3]=1.[CH:11]1(N=C=NC2CCCCC2)[CH2:16]CCC[CH2:12]1>CN(C)C=O>[CH2:2]([OH:1])[CH3:3].[CH:11]([O:1][CH:2]([CH3:3])[CH3:10])([CH3:16])[CH3:12]

Participants

Conditions

Temperature: 5 °C

Procedure

Then, at 20° C., 18.3 g (0.12 mol) of hydroxybenzotriazole (HOBT), 23.7 g (0.109 mol) of N-4-trifluoromethylbenzyl-N-n-propylamine and 25.6 g (0.125 mol) of dicyclohexyl-carbodiimide (DCCI) and a further 250 ml of dimethylformamide (DMF) were added. The mixture was left to react for 24 hours. It was then cooled to 5° C. and filtered. 500 ml of water were added to the filtrate and it was extracted with ethyl acetate. The combined organic phases were washed with water and saturated sodium hydrogen carbonate solution, dried with magnesium sulphate and filtered over kieselguhr/char-coal. After working up in the usual way, 50 g of colourless crystals of the title compound are obtained by crystallisation from ethanol/diisopropylether (1:1). The 3H-PAF-receptor bonding--determined using human thrombocytes--is Ki =1.8 nMol/liter. (The method used is described for example in European Patent Application 368 175).

Workup

waitThe mixture was left
customto react for 24 hours
filtrationfiltered
addition500 ml of water were added to the filtrate and it
extractionwas extracted with ethyl acetate
washThe combined organic phases were washed with water and saturated sodium hydrogen carbonate solution
dry with materialdried with magnesium sulphate
filtrationfiltered over kieselguhr/char-coal

Sources & evidence

ORD record: ord-ca2cdcfad3ee4f1285418e0b70278f44
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05698552

Reaction notes

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