Triethylamine → N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide

HRID 1886741

Reaktionsgleichung

Reaktionsgleichung von HRID 1886741
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].[OH:8]N1C(=O)CCC1=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23](O)[CH3:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[OH:8][CH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 857534-Amino-alpha-methylbenzenemethanolHCID 86640145N-hydroxysuccinimide-(4-pentynoate)

Produkt 1

HCID 58427477N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-hydroxysuccinimide-(4-pentynoate) (Ref: Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C. J.; Russell, T. P.; Wu, P.; Fokin, V. V., Structurally Diverse Dendritic Libraries: A Highly Efficient Functionalization Approach Using Click Chemistry. Macromolecules 2005, 38, (9), 3663-3678.) (200 mg, 1.0 mmol) and p-aminophenylethanol (125 mg, 0.9 mmol) were dissolved in 2 mL of dichloromethane together with triethyl amine (140 μL, 1.0 mmol), and 5 drops of dimethyl formamide. The reaction mixture was stirred at room temperature for 2 hours. The crude reaction product was concentrated, dissolved in 10 mL of ethyl acetate and washed with 5 mL of water followed by, 5 mL of 0.5 M HCl (aq.), 5 mL of 10 NaHCO3 (aq.) and finally 5 mL of water. The organic phase was dried with MgSO4, filtered, and the solvent was evaporated. The product was further purified by column chromatography on silica gel eluting with a gradient of toluene (T) and ethyl acetate (E) from 4:1 to 1:2 (T:E). The product N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide was characterized by NMR and MALDI-TOF.

Aufarbeitung

  1. customThe crude reaction product
  2. concentrationwas concentrated
  3. dissolutiondissolved in 10 mL of ethyl acetate
  4. washwashed with 5 mL of water
  5. dry with materialThe organic phase was dried with MgSO4
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe product was further purified by column chromatography on silica gel eluting with a gradient of toluene (T) and ethyl acetate (E) from 4:1 to 1:2 (T:E)

Quellen und Nachweise

ORD-Eintrag
ord-51dba3c42d9742caa5f52dc5cdc9f010
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501212B2

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