Spermine → HCID 14622100, compound

HRID 1587451Notes

Reaction equation

HRID 1587451 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.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:4]=[CH:5][C:6]([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])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1103SpermineHCID 76904-Methoxyphenylacetic AcidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 14622100HCID 14622100, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

According to the General Procedure using 4-methoxyphenylacetic acid (83 mg, 0.50 mMol), dicyclohexylcarbodiimide (56 mg, 0.27 mMol), and spermine (201 mg, 0.99 mMol) in DME (4 ml), activation during 2.5 h and coupling over 48 h. The product was eluted over silica gel with the lower layer of dichloromethane/methanol/0.880 ammonia solution (4:1:1). The desired amide was in fractions 16-25 and was homogeneous when monitored by tlc on silica (CH2Cl2 /MeOH/NH4OH lower layer, 4:1:1), Rf =0.07, (30 mg, 32%), lyophilisation gave 21 mg of a colourless, viscous oil whose spectroscopic data include: pmr (90 MHz, 2H2O) 1.4-1.8 (m, 8H, 4×CH2 --CH2), 2.4-2.9 (m, 10H, 5×CH2 --N), 3.3 (t, J=7, 2H, CON2H--CH2 --CH2), 3.5 (s, 2H, Ar--CH2 --CO), 3.83 (s, 3H, OCH3), 6.8-6.95 (m, 2H, 2×ArH 3,5), and 7.1-7.3 (m, 2H, 2×ArH 2,6)ppm.

Workup

  1. customduring 2.5 h
  2. washThe product was eluted over silica gel with the lower layer of dichloromethane/methanol/0.880 ammonia solution (4:1:1)
  3. customgave 21 mg of a colourless, viscous oil whose spectroscopic data

Sources & evidence

ORD record
ord-08c1c60065544e27bed9a93f562816b6
Source dataset
uspto-grants-1993_06
Patent number
US05218000

Reaction notes

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