Hydrochloric Acid → HCID 70429691, compound

HRID 1982714Notes

Reaction equation

HRID 1982714 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[CH2:19][C:20]([NH2:22])=[O:21].[C:23](OCC)(=[O:29])[C:24](OCC)=[O:25].CC(C)([O-])C.[K+].Cl>CN(C)C=O.O>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[C:19]1[C:20](=[O:21])[NH:22][C:24](=[O:25])[C:23]=1[OH:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 13030807HCID 13030807, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 70429691HCID 70429691, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a nitrogen atmosphere, (+)-(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)acetamide (19.8 g., 0.0582 mole) and diethyl oxalate (9.14 g., 0.0626 mole) are dissolved in dimethylformamide (100 ml.) and stirred in an ice bath. Potassium tert. butoxide (15.2 g, 0.136 mole) is added in two portions at a 10 minute interval. The reaction mixture is stirred at 25° C. for 18 hours, poured into water (600 ml) acidified with hydrochloric acid, extracted with ether, washed with water and brine and dried over MgSO4. Evaporation of the ether at reduced pressure gives (+)3-(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-dione as the hemietherate in the form of a foam. Upon drying at reduced pressure, the analysis of the hemietherate is as follows:

Workup

  1. stirringThe reaction mixture is stirred at 25° C. for 18 hours
  2. extractionextracted with ether
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the ether at reduced pressure

Sources & evidence

ORD record
ord-7251bb91bd4846e48a807f8b2b9fb007
Source dataset
uspto-grants-1986_06
Patent number
US04596821

Reaction notes

Loading…