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

HRID 1033596
Notes
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Reaction equation

HRID 1033596 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344Dichloromethane
Solvent

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 pate 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-6eb43d06abc048dab26978b800eb254f
Source dataset
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05310959

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes