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

HRID 583104
Notes
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Reaction equation

HRID 583104 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 11219914benzyl N-[(3-hydroxy-4-methoxyphenyl)methyl]carbamate

Product 1

HCID 19689423N-benzyloxycarbonyl-3-(2,3-epoxypropyloxy)-4-methoxybenzylamineYield 108.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. distillationAfter distilling off the solvent under reduced pressure
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed sequentially with an aqueous potassium carbonate solution and with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes