Hydrochloric Acid → 3-[3-(4-{[6-([(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)phenyl]imidazolidine-2,4-dione

HRID 857112Notes

Reaction equation

HRID 857112 reaction equation
C([N:8]([CH2:33][C@@H:34]([C:36]1[CH:47]=[CH:46][C:39]2[O:40]C(C)(C)[O:42][CH2:43][C:38]=2[CH:37]=1)[OH:35])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]#[C:19][C:20]1[CH:21]=[C:22]([N:26]2[C:30](=[O:31])[CH2:29][NH:28][C:27]2=[O:32])[CH:23]=[CH:24][CH:25]=1)C1C=CC=CC=1.Cl>C(O)(C)C.CCOC(C)=O.[OH-].[OH-].[Pd+2]>[OH:35][C@H:34]([C:36]1[CH:47]=[CH:46][C:39]([OH:40])=[C:38]([CH2:43][OH:42])[CH:37]=1)[CH2:33][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([N:26]2[C:30](=[O:31])[CH2:29][NH:28][C:27]2=[O:32])[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 693447783-(3-{4-[(6-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione

Product 1

HCID 98710963-[3-(4-{[6-([(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)phenyl]imidazolidine-2,4-dioneYield 38.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 22055037Isopropanol ethyl acetateSolvent

Procedure

A solution of 3-(3-{4-[(6-{benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6yl)-2-hydroxyethyl]amino}hexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione (9.05 g) in a mixture of isopropanol-EtOAc (9:1, 200 ml) was hydrogenated over Pearlman's catalyst (1.8 g). After 2 days aqueous 2M HCl (10 ml) was added and the mixture was hydrogenated for a further 2 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on Biotage eluting with dichloromethane-isopropanol-880 ammonia (34:7:1) to give the title compound (2.8 g) LCMS RT=2.34 min ES+ve 514 (MH)+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on Biotage
  4. washeluting with dichloromethane-isopropanol-880 ammonia (34:7:1)

Sources & evidence

ORD record
ord-b689597a51874cdba3de0d62c2ad26b1
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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