Water → Methyl 4[((tert-butoxycarbonyl)[2-[(5-phenylpentyl)oxy]-phenethyl]amino)-methyl]benzoate

HRID 2110243Notes

Reaction equation

HRID 2110243 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29]1([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]Br)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[C:1]([O:5][C:6]([N:8]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 285561(5-Bromopentyl)benzeneHCID 22014997Methyl 4-{[(tert-butoxycarbonyl)-(2-hydroxyphenethyl)-amino]methyl}benzoate

Product 1

HCID 22015039Methyl 4[((tert-butoxycarbonyl)[2-[(5-phenylpentyl)oxy]-phenethyl]amino)-methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.78 g (4.63 mmol) of methyl 4-{[(tert-butoxycarbonyl)-(2-hydroxyphenethyl)-amino]methyl}benzoate from Ex.V.2, 1.05 g (4.63 mmol) of 5-phenyl-1-bromopentane and 0.77 g (5.55 mmol) of potassium carbonate in 15 ml of acetonitrile are heated at reflux for 18 hours. The reaction mixture is poured into water, extracted with ethyl acetate and dried over magnesium sulphate and the solvent is distilled off under reduced pressure. A solid is obtained which is reacted further without purification.

Workup

  1. temperatureat reflux for 18 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customA solid is obtained which
  6. customis reacted further without purification

Sources & evidence

ORD record
ord-075d8e8e2eb54ca1a537d49746db75a6
Source dataset
uspto-grants-2009_04
Patent number
US07517896B2

Reaction notes

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