4-Methylmorpholine → 1-[[3-(acetylmercapto)-1-oxopropyl]amino]-L-proline

To a suspension of 3.9 g. of N-amino-L-proline and 6.06 g. of N-methylmorpholine in 200 ml. of dimethylacetamide is added 4.98 g. of 3-acetylthiopropionyl chloride. The temperature of the reaction mixture rises to 34° spontaneously. The reaction mixture is then heated at 90° for 5 hours and allowed to cool to room temperature overnight. The crystalline solid, N-methylmorpholine hydrochloride, is removed by filtration and the filtrate concentrated under reduced pressure. The residue is dissolved in a minimum amount of 20% hydrochloric acid and the aqueous solution is then extracted with 3×150 ml. of ethyl acetate. The ethyl acetate extracts are combined, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to yield the desired N-[[3-(acetylmercapto)-1-oxopropyl]amino]-L-proline.

1. additionTo a suspension of 3.9 g
2. customrises to 34°
3. temperatureThe reaction mixture is then heated at 90° for 5 hours
4. customThe crystalline solid, N-methylmorpholine hydrochloride, is removed by filtration
5. concentrationthe filtrate concentrated under reduced pressure
6. dissolutionThe residue is dissolved in a minimum amount of 20% hydrochloric acid
7. extractionthe aqueous solution is then extracted with 3×150 ml
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-590e3afa0847466f9f6afe4e9d7a269a

Source dataset

uspto-grants-1988_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04734420