Penicillamine → HCID 21304723, Verbindung

Temperatur

0 °C

A solution of D-penicillamine (0.5 g, 3.35 mmol) in methanol (5 mL) was cooled to 0° C. and crushed sodium hydroxide (0.28 g, 6.87 mmol) was added to give a clear solution. 2-Bromoethanol (0.26 mL, 3.71 mmol) was added and stirred at 0° C. for 1 h and at room temperature for an additional 1.5 h. The reaction was concentrated, and the oily residue was dissolved in 3 mL water and 6 mL DMF and stirred with sodium carbonate (0.82 g 7.2 mmol) and 4-butynyloxy-benzenesufonyl chloride (0.78 g, 3.18 mmol) at room temperature overnight. The reaction was concentrated and the residue was extracted with ethyl acetate and water. The aqueous layer was acidified to pH˜3 with concentrated HCl and extracted with ethyl acetate. The second ethyl acetate extract was washed with water and brine, dried over sodium sulfate, filtered and concentrated to obtain 1.2 g of N-{[4-(2-butynyloxy)phenyl]sulfonyl}-3-[(2 hydroxyethyl)sulfanyl]valine as an oil. Yield 89.6%. Electrospray Mass Spec 400.1 (M−H)−.

1. additionwas added
2. customto give a clear solution
3. concentrationThe reaction was concentrated
4. dissolutionthe oily residue was dissolved in 3 mL water
5. concentrationThe reaction was concentrated
6. extractionthe residue was extracted with ethyl acetate and water
7. extractionextracted with ethyl acetate
8. extractionThe second ethyl acetate extract
9. washwas washed with water and brine
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated

ORD-Eintrag

ord-c2d6e755309443bc8ad219f6961bfa51

Quelldatensatz

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06812227B2