2-hydroxyimino-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl ester → Ethyl 2-amino-3-(5-bromo-1H-indol-3-YL)propanoate

HRID 2104213Notes

Reaction equation

HRID 2104213 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5](=[N:17]O)[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[NH:9][CH:8]=1)[CH3:2]>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH2:17])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[NH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 578059932-hydroxyimino-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl ester

Product 1

HCID 14828752Ethyl 2-amino-3-(5-bromo-1H-indol-3-YL)propanoateYield 109.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (3.30 g, 50.4 mmol) was added portionwise to a stirred solution of 2-hydroxyimino-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl ester (4.10 g, 12.61 mmol) in acetic acid (100 mL) over 30 min. After stirring overnight, the mixture was filtered through CELITE® and concentrated. The residue was dissolved in 1 N HCl and re-evaporated to give 4.30 g of the title compound as a crude material. LCMS m/z (ESI) [M−HCl+H]+ calcd for C1-3H15BrN2O2 (Br79) 312.2, found 312.2.

Workup

  1. filtrationthe mixture was filtered through CELITE®
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 1 N HCl
  4. customre-evaporated

Sources & evidence

ORD record
ord-481e25c7d82b4ac7a6e2558da09fd870
Source dataset
uspto-grants-2009_08
Patent number
US07576222B2

Reaction notes

Loading…