Spermine → HCID 14622099, compound

HRID 1587450Notes

Reaction equation

HRID 1587450 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=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]>COCCOC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([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:12]

Participants

5

Reactant 3

HCID 1103SpermineHCID 71342-Methoxyphenylacetic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 14622099HCID 14622099, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

According to the General Procedure using 2-methoxyphenylacetic acid (81 mg. 0.49 mMol), dicyclohexylcarbodiimide (53 mg, 0.26 mMol), and spermine (201 mg, 0.99 mMol) in DME (4 ml), activation during 2.5 h and coupling over 48 h. The produce was eluted over silica gel with the lower layer of dichloromethane/methanol/0.880 ammonia solution (2:1:1). The desired amide was in fractions 6-10 and was homogeneous when monitored by tlc on silica (CH2Cl2 /MeOH/NH4OH lower layer, 2:1:1), Rf =0.25, (28 mg, 31%), lyophilisation gave 16 mg of a colourless, viscous oil whose spectroscopic data include: pmr (90 MHz, 2H2O) 1.35-1.85 (m, 8H, 4×CH2 --CH2), 2.4-2.9 (m, 10H, 5×CH2 --N), 3.25 (t, J=7, 2H, CON2H--CH2 --CH2), 3.5 (s, 2H, Ar--CH2 --CO), 3.83(s, 3H, OCH3), 6.75-7.05 (m, 2H, 2×ArH 3,5), and 7.15-7.35 (m, 2H, 2×ArH 4,6)ppm.

Workup

  1. customduring 2.5 h
  2. washThe produce was eluted over silica gel with the lower layer of dichloromethane/methanol/0.880 ammonia solution (2:1:1)
  3. customgave 16 mg of a colourless, viscous oil whose spectroscopic data

Sources & evidence

ORD record
ord-f00e4627061f4be0b287a3882cc69943
Source dataset
uspto-grants-1993_06
Patent number
US05218000

Reaction notes

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