4-Hydroxybenzoic Acid → HCID 14622106, compound

HRID 1587447Notes

Reaction equation

HRID 1587447 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:26][CH2:27][CH2:28][CH2:29][NH:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37][CH2:38][NH2:39]>COCCOC.CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:39][CH2:38][CH2:37][CH2:36][NH:35][CH2:34][CH2:33][CH2:32][CH2:31][NH:30][CH2:29][CH2:28][CH2:27][NH2:26])=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 1103SpermineHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 14622106HCID 14622106, compound

Reagents, catalysts & solvents 1

HCID 18463208dimethoxyethane N,N-dimethylformamideSolvent

Procedure

According to the General Procedure using 4-hydroxybenzoic acid (80 mg, 0.58 mMol), dicyclohexylcarbodiimide (125 mg, 0.61 mMol), and spermine (430 mg, 2.13 mMol) in DME/DMF (4 ml, 3:1), activation during 3 h and coupling over 48 h. The product was eluted over silica gel with dichloromethane/methanol/0.880 ammonia solution (2:2:1). The desired amide was in fractions 8-12 and was homogeneous when monitored by tic on silica (CH2Cl2 /MeOH/NH4OH, 2:2:1), Rf =0.29, (23 mg, 12%), lyophilisation gave 7 mg of a colourless, viscous oil whose spectroscopic data include: pmr (90 MHz, 2H2O) 1.4-1.9 (m, 8H, 4×CH2 --CH2), 2.5-2.9 (m, 10H, 5×CH2 --N), 3.25 (t, J=7, 2H, CON2H--CH2 --CH2) 6.6-6.9 (m, 2H, 2×ArH 3,5), and 7.0-7.3 (m, 2H, 2×ArH2,6)ppm; M+1 323 (FAB matrix m-nitrobenzyl alcohol) C17H30N4O2 requires M+ 322).

Workup

  1. customduring 3 h
  2. washThe product was eluted over silica gel with dichloromethane/methanol/0.880 ammonia solution (2:2:1)
  3. customgave 7 mg of a colourless, viscous oil whose spectroscopic data

Sources & evidence

ORD record
ord-65aeb1cbf26349779eb81b6914269137
Source dataset
uspto-grants-1993_06
Patent number
US05218000

Reaction notes

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