Penicillamine → HCID 131722540, compound

Temperature

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 the reaction was stirred at 0° C. for 1 hour and then at room temperature for an additional 1.5 hours. The solvent was evaporated 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. After evaporating the solvent, the residue was diluted with ethyl acetate and water. The aqueous layer was acidified to pH˜3 with concentrated HCl and extracted with dichloromethane. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated to obtain 1.2 g of (2S)-2-{[4-(2 butynyloxy)phenyl]sulfonyl}amino)-3-[(2-hydroxyethyl)sulfanyl]-3-methylbutanoic acid as an oil. Yield 89.6%. Electrospray Mass Spec 400.1 (M−H)−.

1. additionwas added
2. customto give a clear solution
3. waitat room temperature for an additional 1.5 hours
4. customThe solvent was evaporated
5. dissolutionthe oily residue was dissolved in 3 mL water
6. customAfter evaporating the solvent
7. additionthe residue was diluted with ethyl acetate and water
8. extractionextracted with dichloromethane
9. washThe organic layer was washed with water and brine
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-8bc24293714145edbdb065f3d198d6e2

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06716833B2