Benzyl N-(4-aminobutyl)carbamate → Ethyl 2-(4-benzyloxycarbonylaminobutyl)aminomethyl-4-phenylbutyrate

HRID 978429Notes

Reaction equation

HRID 978429 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([C:25](=[CH2:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:31][CH:25]([CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2783677Benzyl N-(4-aminobutyl)carbamateHCID 11117162Ethyl alpha-(phenethyl)acrylate

Product 1

HCID 20203289Ethyl 2-(4-benzyloxycarbonylaminobutyl)aminomethyl-4-phenylbutyrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 20 g of 4-benzyloxycarbonylamino-1-butylamine, 21.04 g of ethyl α-(phenethyl)acrylate and 200 ml of ethanol was stirred at room temperature for 8 days and evaporated to dryness. The residue was dissolved in ethyl ether and the solution was extracted three times with 100 ml of 2N hydrochloric acid. The aqueous layer was basified with 2N sodium hydroxide and extracted three times with methylene chloride, dried over magnesium sulfate and evaporated to give the ethyl 2-(4-benzyloxycarbonylaminobutyl)aminomethyl-4-phenylbutyrate having signals in the NMR spectrum at δ=7.4, 7.25, and 5.1 ppm.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in ethyl ether
  3. extractionthe solution was extracted three times with 100 ml of 2N hydrochloric acid
  4. extractionextracted three times with methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-9c2338b2512946f8b623353ee77a3dfe
Source dataset
uspto-grants-1987_05
Patent number
US04665087

Reaction notes

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