Glycine methyl ester hydrochloride → HCID 178501583, compound

HRID 1034410Notes

Reaction equation

HRID 1034410 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Br:17])=[NH:10].Cl.[CH3:19][O:20][C:21](=[O:24])[CH2:22]N>CO>[CH3:19][O:20][C:21](=[O:24])[CH2:22]/[N:10]=[C:9](/[C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[NH2:1])\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Br:17]

Participants

4

Reactant 2

HCID 122755Glycine methyl ester hydrochlorideHCID 19022669HCID 19022669, compound

Product 1

HCID 178501583HCID 178501583, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 139.5 g (0.446 moles) of (2-amino-5-fluorophenyl)(2-bromophenyl)methanimine, 69.9 g (0.557 moles) of glycine methyl ester hydrochloride and 1.68 L of methanol was stirred at reflux for 5 hours under nitrogen. The solvent was then removed by evaporation under vacuum and the yellow, residual solid was partitioned between 1.4 L of methylene chloride and 1.4 L of saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with 0.5 L of methylene chloride. The combined organic extracts were dried with Na2SO4, filtered, and concentrated under vacuum. The residue was redissolved in 0.5L of methylene chloride and concentrated to a dark yellow semi-solid (156.6 g). This solid was recrystallized from 400 mL of 1:3 EtOAc/Hexane to give 72.8 of (Z)-N-[(2-Amino-5-fluorophenyl)(2-bromophenyl)methylene]glycine methyl ester).

Workup

  1. temperatureat reflux for 5 hours under nitrogen
  2. customThe solvent was then removed by evaporation under vacuum
  3. customthe yellow, residual solid was partitioned between 1.4 L of methylene chloride and 1.4 L of saturated NaHCO3 solution
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with 0.5 L of methylene chloride
  6. dry with materialThe combined organic extracts were dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. dissolutionThe residue was redissolved in 0.5L of methylene chloride
  10. concentrationconcentrated to a dark yellow semi-solid (156.6 g)
  11. customThis solid was recrystallized from 400 mL of 1:3 EtOAc/Hexane

Sources & evidence

ORD record
ord-2eb7f0ab32e74a5dafe8fe5c6e901685
Source dataset
uspto-grants-1994_05
Patent number
US05317018

Reaction notes

Loading…