Spermine → HCID 54494747, compound

HRID 1587448Notes

Reaction equation

HRID 1587448 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([OH:9])=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:28][CH2:29][CH2:30][CH2:31][NH:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][CH2:38][CH2:39][CH2:40][NH2:41]>ClCCl>[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([NH:41][CH2:40][CH2:39][CH2:38][NH:37][CH2:36][CH2:35][CH2:34][CH2:33][NH:32][CH2:31][CH2:30][CH2:29][NH2:28])=[O:9]

Participants

5

Reactant 3

HCID 1103SpermineHCID 10868DicyclohexylcarbodiimideHCID 114963-(3-Hydroxyphenyl)-2-propenoic acid

Product 1

HCID 54494747HCID 54494747, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the General Procedure using 3-hydroxycinnamic acid (160 mg, 0.97 mMol), dicyclohexylcarbodiimide (226 mg, 1.10 mMol), and spermine (400 mg, 1.98 mMol) in dichloromethane (6 ml), activation during 2 h and coupling over 21 h. The product was eluted over silica gel with dichloromethane/methanol/0.880 ammonia solution (4:2:1). The desired amide was in fractions 15-22 and was homogeneous when monitored by tlc on silica (CH2Cl2 /MeOH/NH4OH, 4:2:1), Rf =0.22, (108 mg, 32%), lyophilisation gave 90 mg of a yellow viscous gum whose spectroscopic data include: UVmax 213 (emax 3 500), 230sh and 375 (emax 3 800) nm; pmr (90 MHz, 2H2O) 1.4-2.0 (m, 8H, 4×CH2 --CH2), 2.6-3.0 (m, 10H, 5×CH2 --N), 3.35 (t, J=7, 2H, CON2H--CH2 --CH2), 6.4 (d, J=16, 1H, CH=CH--CO), 3.55 (s, 2H, Ar--CH2 --CO), 6.6-6.9 (m, 3H, 3×ArH 2,4,6), and 7.2-7.6 (m, 2H, ArH 5 and ArCH=CH)ppm; M+1 349 (FAB matrix m-nitrobenzyl alcohol) C19H32N4O2 requires M+ 348).

Workup

  1. customduring 2 h
  2. washThe product was eluted over silica gel with dichloromethane/methanol/0.880 ammonia solution (4:2:1)

Sources & evidence

ORD record
ord-f3b407908547468c949a730ede88e3a1
Source dataset
uspto-grants-1993_06
Patent number
US05218000

Reaction notes

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