Formaldehyde → 3-(Benzotriazol-1-ylmethylbenzylamino)propionic acid ethyl ester

HRID 451555Notes

Reaction equation

HRID 451555 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[CH2:10]([NH:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:25]=O>CO>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][CH2:18][N:17]([CH2:25][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:24]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 90196N-(Phenylmethyl)-beta-alanine ethyl esterHCID 178418385HCID 178418385, compound

Product 1

HCID 594427333-(Benzotriazol-1-ylmethylbenzylamino)propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1H-benzo[d][1,2,3]triazole (5.46 g, 45.8 mmol) in MeOH (32 mL) at 0° C. were added ethyl 3-(benzylamino)propanoate (10 g, 45.8 mmol) and an aqueous solution of formaldehyde (36%, 4.56 mL, 59.6 mmol). The reaction mixture was warmed to room temperature and stirred for 12 hours. The solvent was evaporated and the residue was purified by flash-chromatography over 330 g flash pack using gradient EtOAc/Heptane 5-50% over 40 minutes. The title compound was obtained as colorless oil (12.62 g, 81%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash-chromatography over 330 g flash pack
  3. customover 40 minutes

Sources & evidence

ORD record
ord-1e51d864eeec4396b1a95c2a8636a14c
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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