Potassium Acetate → ethyl N-[[5-(3-bromobenzoyl)-2-nitrophenyl]methyl]glycine

HRID 1588077Notes

Reaction equation

HRID 1588077 reaction equation
C([O-])(=O)C.[K+].Cl.[CH2:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])[CH3:8].[Br:14][C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[C:18]([C:20]1[CH:21]=[CH:22][C:23]([N+:28]([O-:30])=[O:29])=[C:24]([CH:27]=1)[CH:25]=O)=[O:19].[B-]C#N.[Na+]>C(O)C>[CH2:7]([N:9]([CH2:25][C:24]1[CH:27]=[C:20]([C:18](=[O:19])[C:17]2[CH:31]=[CH:32][CH:33]=[C:15]([Br:14])[CH:16]=2)[CH:21]=[CH:22][C:23]=1[N+:28]([O-:30])=[O:29])[CH2:10][C:11]([OH:13])=[O:12])[CH3:8]

Participants

6

Reactant 4

HCID 517044Potassium AcetateHCID 151771275-(3-Bromobenzoyl)-2-nitrobenzaldehydeHCID 190114022-(Ethylamino)acetic acid hydrochlorideHCID 20587905Sodium cyanoborohydride [MI]

Product 1

HCID 67883847ethyl N-[[5-(3-bromobenzoyl)-2-nitrophenyl]methyl]glycineYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 58.9 parts of potassium acetate, 100.5 parts of ethyl glycine monohydrochloride and 790 parts of ethanol, there were added 100 parts of 5-(3-bromobenzoyl)-2-nitrobenzaldehyde (prepared following the procedure described in Example 9 or Example 14. After stirring for 1/2 hour, there were added portionwise 9.4 parts of sodium cyanotrihydroborate. Stirring was continued for 1/2 hour at room temperature. The reaction mixture was evaporated and the residue was partitioned between water and dichloromethane. The organic layer was separated, washed with water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /C2H5OH 99:1). The eluent of the desired fraction was evaporated, yielding 71 parts (56.2%) of ethyl N-[[5-(3-bromobenzoyl)-2-nitrophenyl]methyl]glycine (interm. 66).

Workup

  1. customprepared
  2. stirringStirring
  3. waitwas continued for 1/2 hour at room temperature
  4. customThe reaction mixture was evaporated
  5. customthe residue was partitioned between water and dichloromethane
  6. customThe organic layer was separated
  7. washwashed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /C2H5OH 99:1)
  12. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-b131ddc31f904dd59daa6ca97bd40860
Source dataset
uspto-grants-1993_06
Patent number
US05220023

Reaction notes

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