Sodium Sulfate → (S)-1-(2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid

To a 500 mL round-bottomed flask was added benzyl 5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate (3.1 g, 10 mmol), chlorobenzene (30 mL) and the mixture cooled in an ice bath. The trimethylaluminum (25 ml, 50 mmol) was added and the ice bath removed followed by the addition of (S)-2-methyloxirane (0.87 g, 15 mmol). The mixture stirred 1 h and cooled in an ice bath with the addition of THF (60 mL). Sodium sulfate decahydrate (3g) was added to the mixture cautiously (foaming) and the mixture stirred 1 h. Sodium sulfate (10 g) was added and stirred 1 h. The mixture was filtered through celite, washed with 4:1 chloroform/isopropanol and the filtrate concentrated, diluted with chloroform, washed with 1 N HCl and sat. sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by silica gel chromatography eluting with methanol/chloroform to afford the title compound as a foam (1.5 g). MS (ESI pos. ion) m/z: 367 (MH+). Calc'd exact mass for C21H22N2O4: 366.

1. temperaturethe mixture cooled in an ice bath
2. customthe ice bath removed
3. stirringthe mixture stirred 1 h
4. stirringstirred 1 h
5. filtrationThe mixture was filtered through celite
6. washwashed with 4:1 chloroform/isopropanol
7. concentrationthe filtrate concentrated
8. additiondiluted with chloroform
9. washwashed with 1 N HCl and sat. sodium bicarbonate
10. dry with materialThe organic layer was dried over sodium sulfate
11. concentrationconcentrated
12. customThe crude product was purified by silica gel chromatography
13. washeluting with methanol/chloroform

ORDレコード

ord-160a8be336344c218c357b80122f5722

出典データセット

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07759344B2