Acetone → 2-(6-((2-Carboxyethyl)carbamoyl)pyridin-3-yl)-4-chlorobenzoic acid

HRID 405133Notes

Reaction equation

[O-][Mn](=O)(=O)=O.[K+].CC(C)=[O:9].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH:34]=[O:35])=[C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([NH:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[O:25])=[N:22][CH:23]=2)[CH:17]=1>O>[C:29]([CH2:28][CH2:27][NH:26][C:24]([C:21]1[N:22]=[CH:23][C:18]([C:16]2[CH:17]=[C:12]([Cl:11])[CH:13]=[CH:14][C:15]=2[C:34]([OH:35])=[O:9])=[CH:19][CH:20]=1)=[O:25])([OH:31])=[O:30]

Participants

Conditions

Temperature: 50 °C

Procedure

Solid KMnO4 (460 mg, 2.9 mmol) was added to an acetone (14 mL) and water (5 mL) solution of ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate, prepared as described in Example 6, (700 mg, 1.9 mmol) and the resulting mixture was heated to 50° C. After 20 h the resulting mixture was cooled, filtered through CELITE and washed with EtOAc. The aqueous phase was extracted with EtOAc and the combined extracts were washed with water and brine, dried (Na2SO4), and concentrated to yield the title compound, which was used in the next step without further purification.

Workup

customprepared
temperatureAfter 20 h the resulting mixture was cooled
filtrationfiltered through CELITE
washwashed with EtOAc
extractionThe aqueous phase was extracted with EtOAc
washthe combined extracts were washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-3dc193234b77446b954ec90f6874eded
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Reaction notes

Loading…