Methanol → HCID 67741849, compound

HRID 374537Notes

Reaction equation

HRID 374537 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 crystallized 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 crystallized from a mixture of methanol and methyl acetate

Sources & evidence

ORD record
ord-9523519a09794a229996feecc1c36d00
Source dataset
uspto-grants-1996_01
Patent number
US05480910

Reaction notes

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