Triethylamine → N-(3,5-di-t-butyl-4-hydroxycinnamyl)serine methyl ester

HRID 487131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 487131
[C:1]([C:5]1[CH:6]=[C:7]([CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])[CH:8]=[CH:9][C:10](O)=O)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:22][O:23][C:24](=[O:29])[C@H:25]([CH2:27][OH:28])[NH2:26].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>ClCCl>[CH3:22][O:23][C:24](=[O:29])[C@H:25]([CH2:27][OH:28])[NH:26][CH2:10][CH:9]=[CH:8][C:7]1[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:15]([OH:16])=[C:14]([C:17]([CH3:18])([CH3:20])[CH3:19])[CH:13]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 998193-(3,5-Ditert-butyl-4-hydroxyphenyl)prop-2-enoic acidHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 54523948N-(3,5-di-t-butyl-4-hydroxycinnamyl)serine methyl esterAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

First, 20 g of 3,5-di-t-butyl-4-hydroxycinnamic acid, 11.2 g of serine methyl ester hydrochloride, 13.6 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 10 ml of triethylamine were added to 300 ml of dichloromethane, and then the mixture was allowed to react for 2 hours at room temperature. After completion of the reaction, this mixture was washed by addition of water, and the dichloromethane was distilled off under reduced pressure. The residue so obtained was separated and purified by column chromatography on silica gel using chloroform as an eluent, thereby obtaining 9.3 g of N-(3,5-di-t-butyl-4-hydroxycinnamyl)serine methyl ester.

Aufarbeitung

  1. customto react for 2 hours at room temperature
  2. customAfter completion of the reaction
  3. washthis mixture was washed by addition of water
  4. distillationthe dichloromethane was distilled off under reduced pressure
  5. customThe residue so obtained
  6. customwas separated
  7. custompurified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1f9588546adb4655b185b9de17e9d700
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294624

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