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Potassium Carbonate → N-palmitoyl-S-[2(R,S)-hydroxyoctadecyl]-(L)-cysteine

HRID 1904038
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1904038
[C:1]([NH:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][SH:21])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[O:25]1[C:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:26]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:1]([NH:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][S:21][CH2:26][CH:27]([OH:25])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12151201L-Cysteine, N-(1-oxohexadecyl)-HCID 202138261,2-Epoxyoctadecene

Produkt 1

HCID 88720815N-palmitoyl-S-[2(R,S)-hydroxyoctadecyl]-(L)-cysteine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

5.6 g of N-palmitoylcysteine, 5 g of 1,2-epoxy-octadecene and 5.35 g of potassium carbonate in 100 ml ethanol are heated in an atmosphere of nitrogen at 80° for 15 hours. After evaporation, HCl is added so as to obtain a pH of about 3 and the mixture is extracted with chloroform. The chloroform extract is washed with water and is then dried with sodium sulfate. After evaporation there is obtained a colorless residue which is recrystallized from ethyl acetate. There are obtained colorless crystals of the N-palmitoyl-S-[2(R,S)-hydroxyoctadecyl]-(L)-cysteine of melting point 96°-98° [α]D20 =+16° (c=0.78, chloroform).

Aufarbeitung

  1. customAfter evaporation, HCl
  2. additionis added so as
  3. customto obtain a pH of about 3
  4. extractionthe mixture is extracted with chloroform
  5. extractionThe chloroform extract
  6. washis washed with water
  7. dry with materialis then dried with sodium sulfate
  8. customAfter evaporation
  9. customthere is obtained a colorless residue which
  10. customis recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b9653f24c63d40849e360c03a413caca
Quelldatensatz
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04439425

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