Thioglycolic Acid → 4-Methyl-2-(s)-[2-(rs)-(4-chlorophenyl)-4-oxo-thiazolidin-3-yl]-pentanoic acid methyl ester

A suspension of (L)-leucine methyl ester (10 g, 55 mmol) and triethylamine (7.7 ml, 55 mmol) in 120 ml of dioxane was stirred at room temperature for 5 minutes. 3 Å molecular sieves were added followed by p-chlorobenzaldehyde (17 g, 121 mmol). The mixture was heated at 80° C. for 4 hrs. Mercaptoacetic acid (14.2 ml, 203.5 mmol) was added to the mixture and the heating was continued for an additional 12 hrs. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate (40 ml) and water (30 ml). The reaction mixture was filtered to remove the molecular sieves. The organic layer was diluted with ethyl acetate (100 ml), washed twice with 60 ml of saturated solution of sodium carbonate, twice with aqueous 1N HCl and once with water. The organic layer was dried with MgSO4 and evaporated to give a residue that was carried out to the next step without further purification.

1. addition3 Å molecular sieves were added
2. temperatureThe mixture was heated at 80° C. for 4 hrs
3. waitthe heating was continued for an additional 12 hrs
4. temperatureThe reaction mixture was cooled to room temperature
5. filtrationThe reaction mixture was filtered
6. customto remove the molecular sieves
7. additionThe organic layer was diluted with ethyl acetate (100 ml)
8. washwashed twice with 60 ml of saturated solution of sodium carbonate, twice with aqueous 1N HCl and once with water
9. dry with materialThe organic layer was dried with MgSO4
10. customevaporated
11. customto give a residue that
12. customwas carried out to the next step without further purification

ORD-Eintrag

ord-99910d95f2264829ac7b7cdd541f92fd

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06713477B1