Tert-Butylamine → HCID 489108, compound

HRID 843163Notes

Reaction equation

HRID 843163 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18]OS(C)(=O)=O)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[C:24]([NH2:28])([CH3:27])([CH3:26])[CH3:25]>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][NH:28][C:24]([CH3:27])([CH3:26])[CH3:25])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 53820479HCID 53820479, compound

Product 1

HCID 489108HCID 489108, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

4-(2-Methanesulfonyloxy-ethoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (20 mg) and tert-butylamine (0.3 ml) were dissolved in THF (2 ml) and stirred overnight at 60° C. The reaction mixture was dissolved in ethyl acetate and washed with saturated ammonium chloride solution and water. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH=10:1 as a developing solvent) to afford 4-(2-tert-butylamino-ethoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (11 mg) as a colorless oil. FAB-MS: m/z 320 (MH+); 1H-NMR (CDCl3): δ 1.20 (9H, s), 1.44 (3H, t, J=7 Hz), 2.75 (3H, s), 3.08 (2H, t, J=5 Hz), 4.23 (2H, t, J=5 Hz), 4.44 (2H, q, J=7 Hz), 6.62 (1H, d, J=8 Hz), 7.11 (1H, d, J=8 Hz), 7.29 (1H, t, J=8 Hz).

Workup

  1. washwashed with saturated ammonium chloride solution and water
  2. dry with materialThe organic solvent was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by preparative thin layer chromatography (

Sources & evidence

ORD record
ord-653cc0ddf19d4cdf833c2939857707d3
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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