Hydrochloric Acid → HCID 23324910, compound

HRID 464726Notes

Reaction equation

HRID 464726 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:9][C:8](=[O:18])[NH:7]1.C[O:21][C:22](=[O:38])[CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[CH:25]1[CH2:29][CH2:28][C:27](=[O:30])[NH:26]1.Cl>[OH-].[Na+]>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([CH:24]([CH:25]2[CH2:29][CH2:28][C:27](=[O:30])[NH:26]2)[CH2:23][C:22]([OH:38])=[O:21])=[CH:36][CH:35]=1.[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([CH:10]2[CH2:9][C:8](=[O:18])[NH:7][CH:6]2[CH2:5][CH2:4][C:3]([OH:19])=[O:2])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 54255244HCID 54255244, compoundHCID 54405235HCID 54405235, compound

Product 2

HCID 23324910HCID 23324910, compoundHCID 23324926HCID 23324926, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 36.7 g of 3-(4-chlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester and β-(4-chlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester in 130 ml of 1 N aqueous sodium hydroxide solution is heated to 60° C. for four hours. Excess aqueous hydrochloric acid (1 N, 140 ml) is added and the solution concentrated under reduced pressure to give β-(4-chlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid and 3-(4-chlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid. The acids are dissolved in 100 ml of acetic anhydride and the solution heated to 90° C. The solution is filtered hot and the filtrate concentrated in vacuo. The oil is chromatographed on silica gel (200-400 mesh) (elution with chloroform) to yield cis-and trans-dihydro-1-(4-chlorophenyl)-1H-pyrrolizine-3,5(2H,6H)diones as a white solid with mp 153°-58° C.

Workup

  1. concentrationthe solution concentrated under reduced pressure

Sources & evidence

ORD record
ord-a53af4d385c54c4e820b0d83978e3fba
Source dataset
uspto-grants-1985_10
Patent number
US04548947

Reaction notes

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