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

HRID 1936486Notes

Reaction equation

HRID 1936486 reaction equation
C[O:2][C:3](=[O:37])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25](=[O:36])[N:26]([CH3:35])[C:27]([CH3:34])=[CH:28][C:29]=2[C:30]([F:33])([F:32])[F:31])=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][CH3:16])=[O:7].[OH-].[Na+]>C(O)C>[CH2:15]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:37])=[O:2])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25](=[O:36])[N:26]([CH3:35])[C:27]([CH3:34])=[CH:28][C:29]=2[C:30]([F:32])([F:33])[F:31])=[CH:20][CH:19]=1)=[O:7])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69715914N-[(2-ethyl-6-methylphenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl ester

Product 1

HCID 69714759N-[(2-ethyl-6-methylphenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanineYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-[(2-ethyl-6-methylphenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl ester (74 mg, 0.14 mmol), and 1 N sodium hydroxide (2 mL, 2 mmol) in ethanol (3 mL) was heated to 40-45 C for 3 h. Then, the ethanol was removed under vacuum and the residue was diluted with water. The aqueous solution was washed with diethyl ether to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted with ethyl acetate. The combined organic extracts were washed with brine solution and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration afforded 68 mg (95% yield) of N-[(2-ethyl-6-methylphenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine (mp 219-221° C.). ES-HRMS m/e calcd for C27H27F3N2O4 (M+Na) 523.1815, found 523.1816.

Workup

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

Sources & evidence

ORD record
ord-951e0a9bb27244adaf43a271da48e952
Source dataset
uspto-grants-2002_05
Patent number
US06388084B1

Reaction notes

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