3-Pyridinecarboxaldehyde → 4-(3-Aminomethylpyridyl)-2-phenylbenzoylmethionine methyl ester

HRID 325222Notes

Reaction equation

HRID 325222 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[CH3:9][O:10][C:11](=[O:33])[C@H:12]([CH2:29][CH2:30][S:31][CH3:32])[NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18](N)=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH3-]C#[N:36].[Na+].C([O-])(O)=O.[Na+]>CO.C(O)(=O)C>[CH3:9][O:10][C:11](=[O:33])[C@H:12]([CH2:29][CH2:30][S:31][CH3:32])[NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([C:2]2[C:3]([CH2:7][NH2:36])=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 18666758N-(4-Amino-2-phenylbenzoyl)methionine methyl ester

Product 1

HCID 206227934-(3-Aminomethylpyridyl)-2-phenylbenzoylmethionine methyl ester

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

A mixture of 3-pyridinecarboxaldehyde (1.0 equivalent), 4-amino-2-phenylbenzoyl methionine methyl ester (1.0 equivalent) and NaCNBH3 (1.0 equivalent) in methanol/acetic acid is stirred until the reaction is judged complete by TLC analysis. The mixture is poured into aqueous NaHCO3 and extracted into ethyl acetate which is dried and evaporated. Chromatography of the residue on silica gel affords the title compound.

Workup

  1. extractionextracted into ethyl acetate which
  2. customis dried
  3. customevaporated

Sources & evidence

ORD record
ord-2109a6782bca4760beba13555b283c0c
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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