N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester → N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine

HRID 1936471Notes

Reaction equation

C[O:2][C:3](=[O:31])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:30])[N:25]([CH3:29])[CH:26]=[CH:27][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]>C(O)C.[OH-].[Na+]>[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:31])=[O:2])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:30])[N:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[CH:19][CH:18]=1)=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (118 mg, 0.269 mmol) in ethanol (6 mL) was added IN aqueous sodium hydroxide solution (4 mL) at room temperature. The resulting solution was heated to 50° C. and stirred for 2 h. Then, the ethanol was removed under vacuum and the residue was diluted with water (25 mL). The aqueous solution was washed with diethyl ether (25 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 afforded 81 mg (71% yield) of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine as a white solid: mp 204-210° C. FAB-HRMS m/e calcd for C23H21ClN2O4 (M+H) 425.1268, found 425.1267

Workup

customThen, the ethanol was removed under vacuum
additionthe residue was diluted with water (25 mL)
washThe aqueous solution was washed with diethyl ether (25 mL)
customto remove any neutral impurities
extractionthe product was extracted into ethyl acetate (2×25 mL)
washThe combined organic extracts were washed with brine solution (50 mL)
dry with materialwere dried over anhydrous magnesium sulfate
filtrationFiltration of the drying agent and concentration

Sources & evidence

ORD record: ord-1e7e1abcc0664c7ab96afb666965d67f
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06388084B1

Reaction notes

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