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

HRID 895903Notes

Reaction equation

HRID 895903 reaction equation
C[O:2][C:3](=[O:32])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25](=[O:31])[N:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[Br:16])=[O:7].O.[OH-].[Li+].CO.C(O)(=O)C>C1COCC1.O>[Br:16][C:9]1[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:32])=[O:2])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25](=[O:31])[N:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[CH:20][CH:19]=1)=[O:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 69717088N-[(2-bromo-5-methoxyphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester

Product 1

HCID 10116963N-[(2-bromo-5-methoxyphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanineYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[(2-bromo-5-methoxyphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (52 mg, 0.104 mmol) in THF (3 mL) was treated with a solution of lithium hydroxide monohydrate (20 mg, 0.47 mmol) in water (1.0 mL). Methanol (0.5 mL) was added to effect a clear solution and the reaction mixture was stirred 18 hr. Acetic acid (0.5 mL) was added, the entire reaction mixture was applied to a 4×30 cm, C-18 reversed phase HPLC column and eluted with a gradient of acetonitrile in water of 5 to 95% over 35 min. The product containing fraction was lyophillyzed to give N-[(2-bromo-5-methoxyphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine (39 mg, 78%) as a white solid. HRMS: Obs. Mass 485.0703 Calcd. Mass 485.0712 (M+H).

Workup

  1. customthe entire reaction mixture
  2. washeluted with a gradient of acetonitrile in water of 5 to 95% over 35 min
  3. additionThe product containing fraction

Sources & evidence

ORD record
ord-1f304c06b6484d8faf994c14e563d8a7
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

Loading…