Spermine → HCID 14622105, compound

HRID 1587446Notes

Reaction equation

HRID 1587446 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.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]>ClCCl>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([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:7]

Participants

5

Reactant 3

HCID 1103SpermineHCID 74203-Hydroxybenzoic AcidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 14622105HCID 14622105, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the General Procedure using 3-Hydroxybenzoic acid (138 mg, 1.00 mMol), dicyclohexylcarbodiimide (226 mg, 1.10 mMol), and spermine (400 mg, 1.98 mMol) in dichloromethane (6 ml), activation during 3 h and coupling over 17 h. The product was eluted over silica gel with dichloromethane/methanol/0.880 ammonia solution (4:2:1). The desired amide was in fractions 8-13 was homogeneous when monitored by tlc on silica (CH2Cl2 /MeOH/NH4OH, 4:2:1), Rf =0.29, (76 mg, 24%), lyophilisation gave 52 mg of a colorless, 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), 6.5-6.8 (m, 3H, 3× ArH 2,4,6), and 7.0-7.3 (m, 1H, ArH 5) ppm; M+1 323 (FAB matrix m-nitrobenzyl alcohol and sodium chloride) C17H30N4O2 requires M+ 322).

Workup

  1. customduring 3 h
  2. washThe product was eluted over silica gel with dichloromethane/methanol/0.880 ammonia solution (4:2:1)
  3. customgave 52 mg of a colorless, viscous oil whose spectroscopic data

Sources & evidence

ORD record
ord-b45dc0059712486cb95b94cad322f711
Source dataset
uspto-grants-1993_06
Patent number
US05218000

Reaction notes

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