Aniline → 2-(Phenylcarbamoyl)acetic acid

To a solution of aniline (13 mL, 143 mmol) in DCM (290 mL) was added TMSCl (18.2 mL, 143 mmol) at room temperature and the reaction mixture was stirred for 1 hour. [Rigo, B.; Fasseur, D.; Cauliez, P. and Couturier, D. Tetrahedron Lett.; 30; 23; 1989; 3073-3076.]. 2,2-Dimethyl-1,3-dioxane-4,6-dione (20.6 g, 143 mmol) was added and combined reaction mixture was stirred overnight at room temperature, poured into saturated NaHCO3 solution and extracted with EtOAc. The aqueous phase was collected, acidified with conc. HCl to pH-3 by addition of 2N HCl and extracted with DCM. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure affording 3-oxo-3-(phenylamino)propanoic acid (1, 16.82 g, 65% yield) as a white solid. MS (m/z): 180.0 (25%) (M+H), 202.0 (100%) (M+Na).

1. customreaction mixture
2. stirringwas stirred overnight at room temperature
3. extractionextracted with EtOAc
4. customThe aqueous phase was collected
5. additionacidified with conc. HCl to pH-3 by addition of 2N HCl
6. extractionextracted with DCM
7. dry with materialThe organic phase was dried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-baa6e897110f425db32b695f5894c54a

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093264B2