3-(3-{4-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)imidazolidine-2,4-dione → 3-[3-(4-{[6-([(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)phenyl]imidazolidine-2,4-dione acetate

HRID 857097Notes

Reaction equation

HRID 857097 reaction equation
[CH3:1][C:2]1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:39])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([N:32]4[C:36](=[O:37])[CH2:35][NH:34][C:33]4=[O:38])[CH:29]=[CH:30][CH:31]=3)=[CH:11][C:5]=2[CH2:4][O:3]1>C(O)(=O)C.O>[C:2]([OH:7])(=[O:3])[CH3:1].[OH:39][C@H:12]([C:10]1[CH:9]=[CH:8][C:6]([OH:7])=[C:5]([CH2:4][OH:3])[CH:11]=1)[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([N:32]2[C:36](=[O:37])[CH2:35][NH:34][C:33]2=[O:38])[CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 693439983-(3-{4-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)imidazolidine-2,4-dione

Product 1

HCID 566821683-[3-(4-{[6-([(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)phenyl]imidazolidine-2,4-dione acetateYield 135.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3-(3-{4-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)imidazolidine2,4-dione (414 mg) in acetic acid (20 ml) and water (5 ml) was heated to 75° C. for 30 min before evaporating to dryness. The residue was purified by chromatography on Biotage (40 g) eluting with CH2Cl2:MeOH:2M NH3 in MeOH (85:10:5). Appropriate fractions were combined and evaporated to dryness. Acetone (10 ml) was added and the mixture was re-evaporated under reduced pressure to give the title compound (290 mg). LCMS RT=2.44 min, ES+ve 514 (MH)+.

Workup

  1. custombefore evaporating to dryness
  2. customThe residue was purified by chromatography on Biotage (40 g)
  3. washeluting with CH2Cl2
  4. customevaporated to dryness
  5. additionAcetone (10 ml) was added
  6. customthe mixture was re-evaporated under reduced pressure

Sources & evidence

ORD record
ord-31a8bf74718743199a18ddae06b64695
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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