Dicyclohexylcarbodiimide → 1-Pyrrolidineacetamide, 3-hydroxy-2-oxo-, (+-)-

1.64 g of dicyclohexylcarbodiimide dissolved in 20 ml of chloroform are added at room temperature to 1.5 g of (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid, 40 ml of chloroform and 0.86 g of N-hydroxysuccinimide. After 4 hours, the solid is filtered, whereupon the filtrate is concentrated and again filtered. The filtrate is evaporated. The residue is treated at room temperature with 40 ml of a saturated solution of ammonia in methanol. The mixture is stirred at room temperature for 5 minutes, 10 ml of ion-free water are then added thereto and the mixture is stirred at room temperature for an additional minutes. The precipitated solid is filtered. The filtrate is evaporated, the residue is stirred in 30 ml of acetonitrile and the crystallized-out product is recrystallized two more times from acetonitrile. There is obtained (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide of melting point 162°-164°.

1. filtrationthe solid is filtered, whereupon the filtrate
2. concentrationis concentrated
3. filtrationagain filtered
4. customThe filtrate is evaporated
5. additionThe residue is treated at room temperature with 40 ml of a saturated solution of ammonia in methanol
6. addition10 ml of ion-free water are then added
7. stirringthe mixture is stirred at room temperature for an additional minutes
8. filtrationThe precipitated solid is filtered
9. customThe filtrate is evaporated
10. stirringthe residue is stirred in 30 ml of acetonitrile
11. customthe crystallized-out product is recrystallized two more times from acetonitrile

ORD record

ord-56ce80e6aa0c4ed4b19a2a8aee4f74cf

Source dataset

uspto-grants-1987_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04650878