Sodium Hydroxide → HCID 10300477, compound

HRID 844865Notes

Reaction equation

HRID 844865 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]([CH2:33][CH3:34])[C:26](=[O:32])[N:27]([CH2:30][CH3:31])[C:28]=2[CH3:29])=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1[C:13]([CH3:14])=[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]([CH3:14])[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]([CH2:33][CH3:34])[C:26](=[O:32])[N:27]([CH2:30][CH3:31])[C:28]=2[CH3:29])=[CH:21][CH:22]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69336700HCID 69336700, compound

Product 1

HCID 10300477HCID 10300477, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3-diethyl-6-methyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester (0.82 mmol, 420 mg) in ethanol (2 mL) was added aqueous 1.0 N sodium hydroxide (1.6 mL) at room temperature. The mixture was heated to 50° C. and the resulting clear solution was stirred for 2 h. The ethanol was removed under reduced pressure and the residue was diluted with water (25 mL) and NaOH (3 mL, 1.0N) to dissolve the sodium salt. The aqueous solution was washed with diethyl ether (30 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted into ethyl acetate (2×25mL). 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 of the filtrate afforded 277 mg (68% yield) of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3-diethyl-6-methyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine as an amorphous white solid. ES-HRMS m/e calcd for C26H28ClN3O5 (M+Na) 520.1611, found 520.1616.

Workup

  1. customThe ethanol was removed under reduced pressure
  2. additionthe residue was diluted with water (25 mL) and NaOH (3 mL, 1.0N)
  3. dissolutionto dissolve the sodium salt
  4. washThe aqueous solution was washed with diethyl ether (30 mL)
  5. customto remove any neutral impurities
  6. extractionthe product was extracted into ethyl acetate (2×25mL)
  7. washThe combined organic extracts were washed with brine solution (50 mL)
  8. dry with materialwere dried over anhydrous magnesium sulfate
  9. filtrationFiltration of the drying agent and concentration of the filtrate

Sources & evidence

ORD record
ord-aeff21f16b344d6d8ab556e3e7b8e2bd
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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