Nitrogen → HCID 17894883, compound

HRID 727560Notes

Reaction equation

HRID 727560 reaction equation
C([O:8][NH:9][C:10](=[O:31])[CH2:11][C:12]1([CH2:27][CH:28]([CH3:30])[CH3:29])[C:16](=[O:17])[N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14](=[O:26])[NH:13]1)C1C=CC=CC=1.N#N>CO.CCOC(C)=O.[OH-].[OH-].[Pd+2]>[OH:8][NH:9][C:10](=[O:31])[CH2:11][C:12]1([CH2:27][CH:28]([CH3:29])[CH3:30])[C:16](=[O:17])[N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14](=[O:26])[NH:13]1

Participants

5

Reactant 2

HCID 947NitrogenHCID 54521488HCID 54521488, compound

Product 1

HCID 17894883HCID 17894883, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of N-benzyloxy-4-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-4-imidazolidineacetamide (85.0 mg, 0.201 mmol) in 25% MeOH/EtOAc is purged with N2, treated with palladium hydroxide on carbon (17 mg, 20% by weight), and placed under a H2 atmosphere (balloon). After 2.5 hours, the reaction mixture is filtered through celite and concentrated under reduced pressure to yield 70 mg of an off-white foam. The material is recrystallized from hot EtOAc/hexane to give 36 mg (54%) of the title compound as a white, powdery solid (mp 145°-147° C.).

Workup

  1. filtrationthe reaction mixture is filtered through celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f1178aef2fc41daa6df2ff039195770
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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