Acetic Acid → 4-{(1R)-2-[(6-{2-[(2,6-Dichlorobenzyl)oxy]ethoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol acetate

HRID 2116946Notes

Reaction equation

HRID 2116946 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C@@H:17]([C:19]1[CH:30]=[CH:29][C:22]2[O:23][C:24]([CH3:28])(C)[O:25][CH2:26][C:21]=2[CH:20]=1)[OH:18].C(O)(=[O:38])C>O>[C:24]([O:23][C:22]1[CH:29]=[CH:30][C:19]([C@@H:17]([OH:18])[CH2:16][NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][C:3]2[C:2]([Cl:1])=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:35])=[CH:20][C:21]=1[CH2:26][OH:25])(=[O:38])[CH3:28]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 46834265(1R)-2-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Product 1

HCID 668451014-{(1R)-2-[(6-{2-[(2,6-Dichlorobenzyl)oxy]ethoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (1R)-2-[(6-{2-[(2,6-dichlorobenzyl)oxy]ethoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (130 mg) in acetic acid (2 ml) and water (1 ml) was heated (oil bath temperature 80°) with stirring for 30 min. The mixture was cooled to 20° and the solvent was evaporated in vacuo. The residue was azeotroped in vacuo with MeOH (2×1 ml) to give the title compound (135 mg). LCMS RT=2.57 min, ES+ve 486 (MH)+, 488 (MH)+, 490 (MH)+.

Workup

  1. temperatureThe mixture was cooled to 20°
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was azeotroped in vacuo with MeOH (2×1 ml)

Sources & evidence

ORD record
ord-9156525a2f194fd0ad0a8ca4984524f0
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

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