Diisopropylethylamine → N-[(2-bromo-5-methoxyphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester

HRID 895902Notes

Reaction equation

HRID 895902 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:22])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:21])[N:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[NH2:6].[Br:23][C:24]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:25]=1[C:26](O)=[O:27].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:2][O:3][C:4](=[O:22])[C@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15](=[O:21])[N:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[CH:12][CH:13]=1)[NH:6][C:26]([C:25]1[CH:29]=[C:30]([O:33][CH3:34])[CH:31]=[CH:32][C:24]=1[Br:23])=[O:27]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 899062-Bromo-5-methoxybenzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 697153224-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester hydrochloride

Product 1

HCID 69717088N-[(2-bromo-5-methoxyphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester hydrochloride (52 mg, 0.16 mmol), 2-bromo-5-methoxybenzoic acid (45 mg, 0.19 mmol), DIEA (140 μL, 0.80 mmol) and HBTU (85 mg, 0.22 mmol) in DMF (3 mL) was stirred at room temperature for 18 hr. The mixture was concentrated, the residue was dissolved in ethyl acetate (15 mL), was washed with 0.5 N HCl (1×5 mL), sat. NaHCO3 (1×5 mL), brine (1×5 mL) and was dried (MgSO4). The residue obtained upon evaporation (85 mg) was chromatographed on 25 g of silica gel, eluting with ethyl acetate to give N-[(2-bromo-5-methoxyphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (54 mg, 68%). HRMS: Obs. Mass 499.0872. Calcd. Mass 499.0869 (M+H)

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate (15 mL)
  3. washwas washed with 0.5 N HCl (1×5 mL), sat. NaHCO3 (1×5 mL), brine (1×5 mL)
  4. dry with materialwas dried (MgSO4)
  5. customThe residue obtained upon evaporation (85 mg)
  6. customwas chromatographed on 25 g of silica gel
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e021c2469c84439792452a5180cdcaa3
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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