Hydrochloric Acid → HCID 70430098, compound

HRID 364355Notes

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])[CH:8]2[OH:12])=[CH:4][C:3]=1CC(N)=O.[C:23]([O:30]CC)(=O)[C:24]([O:26]CC)=O.[CH3:33][C:34](C)([O-:36])C.[K+].Cl.C[N:41](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[CH2:15][CH2:16][CH2:17][CH2:18]3)([CH3:13])[C:8]2([C:33]2[C:34](=[O:36])[NH:41][C:24](=[O:26])[C:23]=2[OH:30])[OH:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

In an atmosphere of dry nitrogen, (6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-hydroxy-2-methyl-1H-inden-5-yl)acetamide (7.8 g., 0.02 mole) diethyl oxalate (3.14 g., 0.0214 mole) and dimethylformamide (40 ml.) is stirred while cooling in an ice bath. Potassium tert.-butoxide (5.2 g., 0.046 mole) is added in two portions at 10 minute intervals. The mixture is then stirred at 25° C. for 18 hours, poured into water, acidified with hydrochloric acid, extracted into ether and the ether extract dried over magnesium sulfate. Evaporation of the ether at reduced pressure gives 3-(6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-hydroxy-2-methyl-1H-inden-yl)-4-hydroxy-1H-pyrrole-2,5-dione as a mixture of two diastereomers. The mixture of two diastereomers is converted to its 1-methylpiperazine salt, m.p. 226-8.

Workup

temperaturewhile cooling in an ice bath
extractionextracted into ether
extractionthe ether extract
dry with materialdried over magnesium sulfate
customEvaporation of the ether at reduced pressure

Sources & evidence

ORD record: ord-56718b4d97b5416da44e3c0bcb8baae0
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04604403

Reaction notes

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