Hydrochloric Acid → HCID 71477751, compound

HRID 527154Notes

Reaction equation

HRID 527154 reaction equation
Cl.O.[C:3]([O:9][C:10]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=1[C:19]1([NH:33][C:34](=[O:39])[CH2:35][CH2:36][CH2:37][CH3:38])[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[N+:29]([O-])=O)[C:20]1=[O:32])(=[O:8])[CH2:4][CH2:5][CH2:6][CH3:7]>C(O)C.[Fe]>[C:3]([O:9][C:10]1[CH:15]=[C:14]([CH:16]([CH3:17])[CH3:18])[CH:13]=[CH:12][C:11]=1[C:19]1([NH:33][C:34](=[O:39])[CH2:35][CH2:36][CH2:37][CH3:38])[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[NH2:29])[C:20]1=[O:32])(=[O:8])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 121341977HCID 121341977, compound

Product 1

HCID 71477751HCID 71477751, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (0.03 g, 0.6 mmol), conc. HCl (0.05 ml), and water (0.5 ml) were added in that order to a solution of 5-isopropyl-2-(4-nitro-1,3-dioxo-2-pentanamido-2,3-dihydro-1H-inden-2-yl)phenyl pentanoate (43 mg, 0.08 mmol) in ethanol (5 ml). The reaction mixture was heated for 1 hrs under reflux. The reaction mixture was hot filtered off, the filtrate was concentrated in a vacuum and purified by column chromatography (ethylacetate:hexane=1:4 to 1:2) to afford the title compound (22 mg, 55%).

Workup

  1. temperatureThe reaction mixture was heated for 1 hrs
  2. temperatureunder reflux
  3. filtrationThe reaction mixture was hot filtered off
  4. concentrationthe filtrate was concentrated in a vacuum
  5. custompurified by column chromatography (ethylacetate:hexane=1:4 to 1:2)

Sources & evidence

ORD record
ord-09604ba109464bd480b756380252ad1f
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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