2-Methoxyethylamine → HCID 57247108, compound

HRID 1779456Notes

Reaction equation

HRID 1779456 reaction equation
C[C:2]1[C:6]2[CH:7]=[C:8]([O:11][CH2:12][CH2:13][NH:14][CH2:15][C@H:16]([OH:25])[CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:26]([OH:28])=O.[CH3:29][O:30][CH2:31][CH2:32][NH2:33]>CO>[CH3:29][O:30][CH2:31][CH2:32][NH:33][C:26]([C:3]1[O:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][NH:14][CH2:15][C@H:16]([OH:25])[CH2:17][O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:7][C:6]=2[CH:2]=1)=[O:28]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 22872447HCID 22872447, compound

Product 1

HCID 57247108HCID 57247108, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-(2-(2(S)-hydroxy-3-phenoxy-propyl-amino)ethoxy)benzofuran-2-carboxylic acid (0.10 g, 0.26 mmol) and 2-methoxyethyl-amine (0.6 mL) in methanol (3 mL) were maintained at reflux temperature for 18 h. The reaction solution was concentrated in vacuo and flash chromatographed on silica gel (5% methanol:chloroform) to afford the title compound as a colorless solid. (92 mg; m.p. 95°-96° C. Analytical calculated for C23H28N2O6.0.25H2O: C, 63.79; H, 6.63; N, 6.47. Found: C, 63.59; H, 6.39; N, 6.34.)

Workup

  1. temperatureat reflux temperature for 18 h
  2. concentrationThe reaction solution was concentrated in vacuo and flash
  3. customchromatographed on silica gel (5% methanol:chloroform)

Sources & evidence

ORD record
ord-43b23b89b8e34f0a8b08bd2f92422b5d
Source dataset
uspto-grants-1997_05
Patent number
US05627200

Reaction notes

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