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

HRID 844883Notes

Reaction equation

HRID 844883 reaction equation
C[O:2][C:3](=[O:35])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:33])[N:25]([CH3:32])[C:26](=[O:31])[N:27]([CH3:30])[C:28]=2[CH3:29])=[C:19]([CH3:34])[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:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:15])[C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:35])=[O:2])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:33])[N:25]([CH3:32])[C:26](=[O:31])[N:27]([CH3:30])[C:28]=2[CH3:29])=[C:19]([CH3:34])[CH:18]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69337580N-[(2,6-dichlorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine methyl ester

Product 1

HCID 10118022N-[(2,6-dichlorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanineYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of N-[(2,6-dichlorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine methyl ester (0.04 mmol, 22 mg) in ethanol (2 mL) was added aqueous 1.0 N sodium hydroxide (0.5 mL) at room temperature. The mixture was stirred for 2 h at room temperature. The ethanol was removed under reduced pressure and the residue was diluted with water (10 mL). The aqueous solution was washed with diethyl ether (20 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted into ethyl acetate (2×15 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 20 mg (93% yield) of N-[(2,6-dichlorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine as an amorphous white solid. ES-HRMS m/e calcd for C23H21Cl2N3O5 [(M-H)+2Na] 548.0725, found 548.0733.

Workup

  1. customThe ethanol was removed under reduced pressure
  2. additionthe residue was diluted with water (10 mL)
  3. washThe aqueous solution was washed with diethyl ether (20 mL)
  4. customto remove any neutral impurities
  5. extractionthe product was extracted into ethyl acetate (2×15 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 of the filtrate

Sources & evidence

ORD record
ord-d52da14d24484466a6e090800dc5bbda
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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