Sodium Hydroxide → [Benzyl-(3-methoxy-benzyl)-amino]-acetic acid

HRID 1687934Notes

Reaction equation

HRID 1687934 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][N:6]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)C.[OH-].[Na+]>C(O)C>[CH2:16]([N:6]([CH2:5][C:4]([OH:23])=[O:3])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13760251ethyl N-(3-methoxybenzyl)benzylaminoethanoate

Product 1

HCID 39385259[Benzyl-(3-methoxy-benzyl)-amino]-acetic acidYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[Benzyl-(3-methoxy-benzyl)-amino]-acetic acid ethyl ester (3.0 g, 9.6 mmol) in ethanol (100 mL) was treated with 4N NaOH (20 mL) and the mixture was stirred at ambient temperature for two hours whereupon HPLC analysis showed completion of the reaction. The ethanol was removed on the rotary evaporator, water (˜20 mL) was added to dissolve solids, the pH was adjusted to 4 (6N HCl) with stirring and the precipitate was collected by filtration, washed with water and dried to constant weight in vacuo to give 2.47 g (90%) of [benzyl-(3-methoxy-benzyl)-amino]-acetic acid as a white solid; 1H NMR (400 MHz, DMSO-d6) δ 12.30 (br s, 1H), 7.35 (m, 4H), 7.25 (m, 2H), 6.93 (m, 2H), 6.82 (d, J=9 Hz, 1H), 3.74 (s, 3H), 3.72 (s, 2H), 3.30 (br s, 2H, 3.17 (s, 2H); MS (m/e) 286 (M+1); mp 177-179° C.

Workup

  1. customcompletion of the reaction
  2. customThe ethanol was removed on the rotary evaporator, water (˜20 mL)
  3. additionwas added
  4. dissolutionto dissolve solids
  5. stirringwith stirring
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with water
  8. customdried to constant weight in vacuo

Sources & evidence

ORD record
ord-9155291640a549fab2e62e6d2ab8f5a4
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…