Triethylamine → HCID 9948873, Verbindung

To a stirred solution of 2-(4-methoxy-phenylsulfanyl)-2-methyl-3-phenyl-propionic acid (0.5 g, 1.65 mmol) and DMF (2 drops) in CH2Cl2 (100 ml) at 0° C., oxalyl chloride (1.0 gm, 8 mmol) was added in a drop-wise manner. After the addition, the reaction mixture was stirred at room temperature for 1 hour. Simultaneously, in a separate flask a mixture of hydroxylamine hydrochloride (2.0 gm, 29 mmol) and triethylamine (5 ml, excess) was stirred in THF:water (5:1, 30 ml) at 0° C. for 1 hour. At the end of 1 hour, the oxalyl chloride reaction mixture was concentrated and the pale yellow residue was dissolved in 10 ml of CH2Cl2 and added slowly to the hydroxylamine at 0° C. The reaction mixture was stirred at room temperature for 24 hours and concentrated. The residue obtained was extracted with chloroform and washed well with water. The product obtained was purified by silica gel column chromatography and eluted with ethyl acetate. The N-hydroxy-2-(4-methoxyphenylsulfanyl)-2-methyl-3-phenyl-propionamide was isolated as a colorless solid. mp 88° C.; Yield, 300 mg, 57%; MS: 318 (M+H)+; 1H NMR (300 MHz, CDCl3): δ1.32 (s, 3H), 3.07 (d, J=11 Hz, 1H), 3.23 (d, J=11 Hz, 1H), 3.79 (s, 3H), 6.83-7.36 (m, 9H).

1. additionAfter the addition
2. concentrationwas concentrated
3. dissolutionthe pale yellow residue was dissolved in 10 ml of CH2Cl2
4. additionadded slowly to the hydroxylamine at 0° C
5. stirringThe reaction mixture was stirred at room temperature for 24 hours
6. concentrationconcentrated
7. customThe residue obtained
8. extractionwas extracted with chloroform
9. washwashed well with water
10. customThe product obtained
11. customwas purified by silica gel column chromatography
12. washeluted with ethyl acetate

ORD-Eintrag

ord-d8e3cfaa030c40058ab907dd7c07b800

Quelldatensatz

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06331563B1