Methanol → HCID 67741849, compound

HRID 1647854Notes

Reaction equation

HRID 1647854 reaction equation
[ClH:1].[OH:2][C@H:3]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:4][NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](N)=[O:17])=[CH:11][CH:10]=1.S(=O)(=O)(O)O.[CH3:30][OH:31]>>[ClH:1].[OH:2][C@H:3]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:4][NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:31][CH3:30])=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 67741842HCID 67741842, compound

Product 1

HCID 67741849HCID 67741849, compound

Procedure

(R)-4-[2-(2-Hydroxy-2-phenylethylamino)ethoxy]phenylacetamide hydrochloride (0.45 g) was heated under reflux in methanol (20 ml) containing concentrated sulphuric acid (0.5 ml) for 18 hours. The mixture was cooled and the solvent evaporated under reduced pressure. The residue was dissolved in dichloromethane (30 ml) and washed successively with water (20 ml), 5% NaHCO3 solution (50 ml) and water (20 ml), dried over MgSO4 and then the solvent was removed under reduced pressure. The residue was dissolved in methyl acetate (20 ml) and treated with a solution of ether saturated with hydrogen chloride. The precipitated solid was crystallised from a mixture of methanol and methyl acetate to give (R)-methyl 4-[2-(2-hydroxy-2-phenylethylamino)ethoxy]phenylacetate hydrochloride (0.25 g), m.p. 181°-183° C.; microanalysis: found, C, 62.6; H, 6.6; N, 3.8; Cl, 9.9%; required for C19H24ClNO4 : C, 62.4; H, 6.6; N, 3.8; Cl, 9.7%; [α]25D =-25.3° (c=0.99 in methanol).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (30 ml)
  4. washwashed successively with water (20 ml), 5% NaHCO3 solution (50 ml) and water (20 ml)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe residue was dissolved in methyl acetate (20 ml)
  8. additiontreated with a solution of ether saturated with hydrogen chloride
  9. customThe precipitated solid was crystallised from a mixture of methanol and methyl acetate

Sources & evidence

ORD record
ord-aefc77d6f79c4fc7812945e2b956a92c
Source dataset
uspto-grants-1995_07
Patent number
US05434184

Reaction notes

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