Sodium Hydroxide → HCID 9890248, compound

HRID 844841Notes

Reaction equation

HRID 844841 reaction equation
C[O:2][C:3](=[O:33])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:32])[N:25]([CH3:31])[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=2)=[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:33])=[O:2])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:24](=[O:32])[N:25]([CH3:31])[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=2)=[CH:21][CH:22]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15908953HCID 15908953, compound

Product 1

HCID 9890248HCID 9890248, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
42.5 °C

Procedure

To a suspension of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester (0.278 mmol, 131 mg) in ethanol (4 mL) was added aqueous 1.0 N sodium hydroxide (3 mL) at room temperature. The mixture was heated to 40-45° C. and the resulting clear solution was stirred for 2-3 h. The ethanol was removed under reduced pressure and the residue was diluted with water (20 mL) and NaOH (3 mL, 1.0N) to dissolve the sodium salt. The aqueous solution was washed with ether (50 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted into ethyl acetate (2×50 mL). The combined organic extracts were washed with brine solution and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the filtrate afforded 107 mg (85%) of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine as a white solid: mp 234-236° C. EI-HRMS m/e calcd for C23H22N3O5Cl (M+H) 456.1326, found 456.1326.

Workup

  1. customThe ethanol was removed under reduced pressure
  2. additionthe residue was diluted with water (20 mL) and NaOH (3 mL, 1.0N)
  3. dissolutionto dissolve the sodium salt
  4. washThe aqueous solution was washed with ether (50 mL)
  5. customto remove any neutral impurities
  6. extractionthe product was extracted into ethyl acetate (2×50 mL)
  7. washThe combined organic extracts were washed with brine solution
  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-d47eea8105ff4f8ea3d6d98357e5fafb
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

Loading…