Triethylamine → Dodecyl glycinate

HRID 54895

Reaktionsgleichung

Reaktionsgleichung von HRID 54895
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:24][C:25](=[O:28])[CH2:26][NH2:27])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C>C(O)(C)C>[NH2:27][CH2:26][C:25]([O:24][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:28]

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 15435490Glycine 1-dodecyl ester tosylate

Produkt 1

HCID 6452634Dodecyl glycinateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A 100 ml round bottom flask equipped with a condenser, addition funnel, thermometer and mechanical stirrer was charged with D-glucono-1,5-1-actone (5.0 g, 0.03 mole) and isopropanol (35 g). The suspension was heated to 50° C. over 15 minutes. A mixture of glycine dodecyl ester p-toluenesulfonate salt (11.7 g, 0.03 mole), triethylamine (2.9 g 0.03 mole) and isopropanol (20 g) were added dropwise over 15 minutes from an addition funnel. The reaction mixture was stirred rapidly for about 2 hrs and then cooled to room temperature. The white product was filtered, washed with chloroform (3×150 ml) and dried under high vacuum at 35° C. giving 7.2 g (61% yield) of N-D-gluconyl dodecyl glycinate with a melting point of 121°-122° C. and 98.6% purity.

Aufarbeitung

  1. customA 100 ml round bottom flask equipped with a condenser, addition funnel
  2. additionwere added dropwise over 15 minutes from an addition funnel
  3. temperaturecooled to room temperature
  4. filtrationThe white product was filtered
  5. washwashed with chloroform (3×150 ml)
  6. customdried under high vacuum at 35° C.

Quellen und Nachweise

ORD-Eintrag
ord-692fbb4d1703430e81b062128869b05d
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624906

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