Sodium Hydroxide → N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine

HRID 844849Notes

Reaction equation

HRID 844849 reaction equation
C[O:2][C:3](=[O:35])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25](=[O:34])[N:26]([CH3:33])[C:27](=[O:32])[N:28]([CH3:31])[C:29]=2[CH3:30])=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[OH-].[Na+]>C(O)C>[CH3:16][O:15][CH2:14][CH2:13][C:8]1([C:6]([NH:5][C@H:4]([C:3]([OH:35])=[O:2])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25](=[O:34])[N:26]([CH3:33])[C:27](=[O:32])[N:28]([CH3:31])[C:29]=3[CH3:30])=[CH:20][CH:19]=2)=[O:7])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69336589HCID 69336589, compound

Product 1

HCID 10116180N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanineYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
42.5 °C

Procedure

To a suspension of N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester (0.273 mmol, 133 mg) in ethanol (3 mL) was added aqueous 1.0 N sodium hydroxide (1.5 mL) at room temperature. The mixture was heated to 40-45° C. and the resulting clear solution was stirred for 15 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 (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 (2×25 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 of the filtrate afforded 121 mg (94% yield) of N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine as an amorphous white solid. FAB-HRMS m/e calcd for C25H33N3O6 (M+H) 472.2448, found 472.2467.

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 (50 mL)
  5. customto remove any neutral impurities
  6. extractionthe product was extracted into ethyl acetate (2×25 mL)
  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-869e31d829644db7a2e7688a55207aa9
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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