HCID 15232945, compound → HCID 18958344, compound

HRID 2255012Notes

Reaction equation

HRID 2255012 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].S(O[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[C:1]1(=[O:11])[N:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 2

HCID 15232945HCID 15232945, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 18958344HCID 18958344, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
110 °C

Procedure

A mixture of potassium phthalimide (5.59 g, 30.2 mmoles) and 200 ml of dried N,N-dimethylformamide was heated to 110° C. To this mixture was added dropwise methyl 20-tosyloxyeicosanoate (10.0 g, 20.1 mmoles) dissolved in 300 ml of N,N-dimethylformamide and the resulting mixture was heated at 110° C. with stirring for 2 hours. After the completion of the reaction, the reaction mixture was treated in the same manner as in Reference Example 2 to give methyl 20-phthalimidoeicosanoate (8.97 g, 95%) having the following properties.

Workup

  1. temperaturethe resulting mixture was heated at 110° C.
  2. customAfter the completion of the reaction
  3. additionthe reaction mixture was treated in the same manner as in Reference Example 2

Sources & evidence

ORD record
ord-09f7b7eeb8264abf8f8ab796d10027c4
Source dataset
uspto-grants-1993_08
Patent number
US05238837

Reaction notes

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