Sodium Hydroxide → HCID 69715313, compound

HRID 895933Notes

Reaction equation

HRID 895933 reaction equation
C[O:2][C:3](=[O:36])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:35])[N:25]([CH3:34])[C:26]([C:30]([F:33])([F:32])[F:31])=[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:36])=[O:2])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:24](=[O:35])[N:25]([CH3:34])[C:26]([C:30]([F:32])([F:33])[F:31])=[CH:27][C:28]=2[CH3:29])=[CH:21][CH:22]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69715186N-[(2,6-dichlorophenyl)carbonyl]-4-[1,4-dimethyl-6-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl ester

Product 1

HCID 69715313HCID 69715313, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
47.5 °C

Procedure

To a suspension of N-[(2,6-dichlorophenyl)carbonyl]-4-[1,4-dimethyl-6-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl ester (243 mg, 0.45 mmol) in ethanol (5 mL) was added 1N aqueous sodium hydroxide solution (1.8 mL) at room temperature. The mixture was heated to 45-50° C. and was stirred for 2 h. Then, the ethanol was removed under vacuum and the residue was diluted with water (20 mL). The aqueous solution was washed with ethyl acetate (50 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted with ethyl acetate (2×50 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 186 mg (79% yield) of N-[(2,6-dichlorophenyl)carbonyl]-4-[1,4-dimethyl-6-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine as an amorphous white solid. ES-HRMS m/e calcd for C24H19Cl2F3N2O4 (M+Na) 549.0567. found 549.0573.

Workup

  1. customThen, the ethanol was removed under vacuum
  2. additionthe residue was diluted with water (20 mL)
  3. washThe aqueous solution was washed with ethyl acetate (50 mL)
  4. customto remove any neutral impurities
  5. extractionthe product was extracted with ethyl acetate (2×50 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-0e76e65836e444708365227dda498f70
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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