1,1'-Carbonyldiimidazole → HCID 19068519, compound

To a stirred solution of 2-acetamido-4-(2-amino-5-chlorophenyl)-4-oxo-butyric acid (0.569 g; 2 mmol) in dry DMF (8 ml), 1,1'-carbonyldiimidazole (0.34 g; 2.1 mmol) was added portionwise at 5°-8° C. under nitrogen. After stirring at 5° C. for 1.5 h, (R)-(-)-2-amino-2-phenylethanol (0.33 g; 2.4 mmol) in dry DMF (6 ml) was added dropwise at 3°-5° C. The reaction was then stirred for 2 h in an ice bath and 16 h at room temperature, quenched with water and extracted with ethyl acetate. The organic layer was washed with water, dried with an. sodium sulfate and concentrated to dryness. The residue was purified by flash-chromatography on silica gel (ethyl acetate:methanol=98:2) to yield 2-acetylamino-4-(2-amino-5-chlorophenyl)-N-(2-hydroxy-1-phenyl-ethyl)-4-oxobutyramide as a yellow solid (0.18 g; 22%; m.p. 212°-215° C.) (pure diastereoisomer with Rf<).

1. stirringThe reaction was then stirred for 2 h in an ice bath and 16 h at room temperature
2. customquenched with water
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with water
5. customdried with an
6. concentrationsodium sulfate and concentrated to dryness
7. customThe residue was purified by flash-chromatography on silica gel (ethyl acetate:methanol=98:2)

ORD record

ord-b2ade4a69b63473ca2d9cafd1622f01b

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05786508