Carbon Dioxide → HCID 14427781, compound

HRID 346310Notes

Reaction equation

HRID 346310 reaction equation
C(O)C.[CH:4]1([CH2:10][C@@H:11]2[NH:15][C:14](=[O:16])[C:13](C(OCC)=O)=[C:12]2[OH:22])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(=O)=O>O>[CH:4]1([CH2:10][C@@H:11]2[NH:15][C:14](=[O:16])[CH2:13][C:12]2=[O:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 702Ethanol2×HCID 867434741H-Pyrrole-3-carboxylic acid, 5-(cyclohexylmethyl)-2,5-dihydro-4-hydroxy-2-oxo-, ethyl ester, (S)-

Product 1

HCID 14427781HCID 14427781, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1 L of 50% ethanol in water is brought to the boiling point in a large beaker and 68.2 g (0.255 mol) of (S)-5-(cyclohexylmethyl)-2,5-dihydro-4-hydroxy-2-oxo-1H-pyrrole-3-carboxylic acid, ethyl ester is added over about 5 minutes (pot temperature is 82°-84° C.). The solid goes into solution as carbon dioxide evolves. The ethanol is allowed to boil-off over a period of one-half hour (pot temperature is 87° C.). The volume is about 750 ml, a slight turbidity develops and crystals separate on cooling to afford 48.5 g of (S)-5-(cyclohexylmethyl)-2,4-pyrrolidinedione after recrystallization from ethyl acetate; mp 165°-167° C.; [α]D23 =-75° (c=1.1% chloroform).

Workup

  1. additionis added over about 5 minutes (pot temperature is 82°-84° C.)
  2. customis allowed to boil-off over a period of one-half hour (pot temperature is 87° C.)
  3. customcrystals separate
  4. temperatureon cooling

Sources & evidence

ORD record
ord-e1879658082b4c6eb631817a0e753fb5
Source dataset
uspto-grants-1991_10
Patent number
US05061808

Reaction notes

Loading…