5,8,11-Eicosatriynoic acid → HCID 13773460, compound

HRID 2352529Notes

Reaction equation

HRID 2352529 reaction equation
[C:1]([OH:22])(=O)[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(N1C=CN=C1)(N1C=CN=C1)=O.[OH:35][CH:36]([CH2:39][OH:40])[CH2:37][NH2:38]>CN(C=O)C.C(Cl)Cl>[OH:35][CH:36]([CH2:39][OH:40])[CH2:37][NH:38][C:1](=[O:22])[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 17815,8,11-Eicosatriynoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 735613-Amino-1,2-propanediol

Product 1

HCID 13773460HCID 13773460, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In the same manner as in the above example, 8 g of 5,8,11-eicosatriynoic acid in 40 cm3 of anhydrous DMF are treated initially with 5.62 g of carbonyldiimidazole. 4.1 cm3 of 2,3-dihydroxypropylamine are then added at 0° C. At the end of the reaction, the reaction mixture is poured into ice-cold water. The precipitated product is drained and dissolved in 300 cm3 of methylene chloride. The solution is dried over sodium sulphate and then concentrated under reduced pressure. The solid obtained is directly recrystallized in acetonitrile. 9 g of N-(2,3-dihydroxypropyl)-5,8,11-eicosatriynamide are thereby obtained in the form of very pale beige crystals of melting point 87° C.

Workup

  1. customAt the end of the reaction
  2. additionthe reaction mixture is poured into ice-cold water
  3. dry with materialThe solution is dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe solid obtained
  6. customis directly recrystallized in acetonitrile

Sources & evidence

ORD record
ord-8c085bf8d7bb45acb650ed46bbf55f71
Source dataset
uspto-grants-1989_10
Patent number
US04877789

Reaction notes

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