Potassium Carbonate → N-benzyloxycarbonyl-3-(2,3-epoxypropyloxy)-4-methoxybenzylamine

HRID 583104Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28]([CH:30]1[O:32][CH2:31]1)Br>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:28][CH:30]2[O:32][CH2:31]2)[CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture comprising 2 g of N-benzyloxycarbonyl-3-hydroxy-4-methoxybenzylamine, 20 ml of dimethylformamide, 1.4 g of potassium carbonate and 1.4 g of epibromohydrin, was stirred at 60° C. overnight. After distilling off the solvent under reduced pressure, the reaction mixture was extracted with ethyl acetate. The obtained organic layer was washed sequentially with an aqueous potassium carbonate solution and with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 2.6 g of the above-identified compound as oily substance.

Workup

distillationAfter distilling off the solvent under reduced pressure
extractionthe reaction mixture was extracted with ethyl acetate
washThe obtained organic layer was washed sequentially with an aqueous potassium carbonate solution and with a saturated sodium chloride aqueous solution
dry with materialdried over anhydrous sodium sulfate
distillationThen, the solvent was distilled off

Sources & evidence

ORD record: ord-50ad98b72cac45f8b4ef3d54ccddbef9
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05929074

Reaction notes

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