3-Pyridinecarboxaldehyde → [4(3-Pyridylmethylamino)-2-phenylbenzoyl]methionine methyl ester

HRID 2121172Notes

Reaction equation

HRID 2121172 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:26])[C@H:5]([CH2:22][CH2:23][S:24][CH3:25])[NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]=O)[CH:28]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH3:2][O:3][C:4](=[O:26])[C@H:5]([CH2:22][CH2:23][S:24][CH3:25])[NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:33][C:29]2[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=2)=[CH:10][C:9]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69612387(4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochloride

Product 1

HCID 10694816[4(3-Pyridylmethylamino)-2-phenylbenzoyl]methionine methyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

(4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochloride (5.0 g, 12.7 mmol), prepared as in Example 192B, and 3-pyridinecarboxaldehyde (1.25 mL, 13.3 mmol) were dissolved in 100 mL 1% acetic acid in methanol. After 10 minutes, sodium cyanoborohydride (0.95 g, 15.9 mmol) was added. After stirring at room temperature 18 hours, the reaction mixture was evaporated and partitioned between 5% NaHCO3 and ethyl acetate. The organic layer was washed with 5% NaHCO3 and brine, dried over Na2SO4, and evaporated to provide [4-(3-pyridylmethylamino)-2-phenylbenzoyl]methionine methyl ester which was used without further purification. MS m/e 450 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.65 (m, 2H), 1.87 (m, 2H), 2.00 (s, 3H), 3.63 (s, 4H), 4.42 (s, 2H), 4.61 (m, 1H), 5.69 (d, J=7 Hz, 1H), 6.50 (d, J=3 Hz, 1H), 6.63 (m, 1H), 7.45 (m, 6H), 7.68 (m, 2H), 8.55 (m, 1H), 8.62 (d, J=3 Hz, 1H).

Workup

  1. customthe reaction mixture was evaporated
  2. custompartitioned between 5% NaHCO3 and ethyl acetate
  3. washThe organic layer was washed with 5% NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-e6ce2dedb36643e1bbddc6e79137bd2e
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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