Spermine → N-(3-Fluoro-4-hydroxyphenylacetyl)-spermine

HRID 1587449Notes

Reaction equation

HRID 1587449 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[OH:8].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.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 1103SpermineHCID 10868DicyclohexylcarbodiimideHCID 680143-Fluoro-4-hydroxybenzeneacetic acid

Product 1

HCID 14622110N-(3-Fluoro-4-hydroxyphenylacetyl)-spermine

Reagents, catalysts & solvents 1

HCID 18463208dimethoxyethane N,N-dimethylformamideSolvent

Procedure

According to the General Procedure using 3-fluoro-4-hydroxyphenylacetic acid (85 mg, 0.50 mMol), dicyclohexylcarbodiimide (106 mg, 0.31 mMol), and spermine (512 mg, 2.53 mMol) in DME/DMF (4 ml, 3:1), activation during 2 h and coupling over 48 h. The product was eluted over silica gel with dichloromethane/methanol/0.880 ammonia solution (4:2:1). The desired amide was in fractions 12-19 and was homogeneous when monitored by tlc on silica (CH2Cl2 /MeOH/NH4OH, 4:2:1), Rf =0.19, (39 mg, 22%), lyophilisation gave 30 mg of a colourless, viscous oil whose spectroscopic data include: pmr (90 MHz, 2H2O) 1.6-2.2 (m, 8H, 4×CH2 --CH2), 2.85-3.2 (m, 10H, 5×CH2 --N), 3.4 (t, J=7, 2H, CON2H--CH2 --CH2), 3.6 (s, 2H, Ar--CH2 --CO), 6.8-7.1 (m, 2H, 2×ArH 5,6), and 7.1 (d, 3 J H--F=11, H, ArH 2)ppm.

Workup

  1. customduring 2 h
  2. washThe product was eluted over silica gel with dichloromethane/methanol/0.880 ammonia solution (4:2:1)
  3. customgave 30 mg of a colourless, viscous oil whose spectroscopic data

Sources & evidence

ORD record
ord-059769ef9f8644b4afd74dc0882d4aee
Source dataset
uspto-grants-1993_06
Patent number
US05218000

Reaction notes

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