Sodium Hydroxide → N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine

HRID 1936476Notes

Reaction equation

HRID 1936476 reaction equation
C[O:2][C:3](=[O:32])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:31])[N:25]([CH3:30])[CH:26]=[CH:27][C:28]=2[CH3:29])=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])=[O:7].[OH-].[Na+]>C(O)C>[Cl:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([Cl:14])[C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:32])=[O:2])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:31])[N:25]([CH3:30])[CH:26]=[CH:27][C:28]=2[CH3:29])=[CH:19][CH:18]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69716202N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester

Product 1

HCID 10139365N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanineYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
42.5 °C

Procedure

To a suspension of N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (20 mg, 0.04 mmol) in ethanol (1 mL) was added 1N aqueous sodium hydroxide solution (0.5 mL) at room temperature. The mixture was heated to 40-45° C. and stirred for 3 h. Then, the ethanol was removed under vacuum and the residue was diluted with water (10 mL). The aqueous solution was washed with diethyl ether (25 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted into ethyl acetate (2×25 mL). The combined organic extracts were washed with brine solution (50 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration afforded 17 mg (89% yield) of N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine as an amorphous white solid. ES-HRMS m/e calcd for C23H20Cl2N2O4 (M+Na) 481.0691, found 481.0699.

Workup

  1. customThen, the ethanol was removed under vacuum
  2. additionthe residue was diluted with water (10 mL)
  3. washThe aqueous solution was washed with diethyl ether (25 mL)
  4. customto remove any neutral impurities
  5. extractionthe product was extracted into ethyl acetate (2×25 mL)
  6. washThe combined organic extracts were washed with brine solution (50 mL)
  7. dry with materialwere dried over anhydrous magnesium sulfate
  8. filtrationFiltration of the drying agent and concentration

Sources & evidence

ORD record
ord-7df5e1928d894d3fa518796a57457acc
Source dataset
uspto-grants-2002_05
Patent number
US06388084B1

Reaction notes

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