Hydrochloric Acid → N-myristoyl-D-alanine

HRID 1196066

Reaktionsgleichung

Reaktionsgleichung von HRID 1196066
[NH2:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3].C(N(CC)CC)C.[C:14]([O-])(=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].S([O-])(OC(C)(C)S(OC1C=CC(O)=CC=1)(=O)=O)(=O)=O.Cl>O>[C:14]([NH:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3])(=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 71080D-AlanineHCID 4075158MyristateHCID 867457864-Hydroxyphenyldimethylsulfomethyl sulfate

Produkt 1

HCID 54463945N-myristoyl-D-alanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

D-alanine 1.78 g (0.02 mol) and triethylamine 2.8 ml (0.02 mol) were dissolved in 60 ml of water. Myristate of 4-hydroxyphenyldimethylsulfomethyl sulfate 9.52 g (0.02 mol) was added to the solution, and the mixture was stirred for 12 hours at room temperature. The solution reacted was adjusted to pH 2 or 3 with 1N-HCl and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and freed of solvent in vacuo. The oily residue obtained was purified by column chromatography (column: 2.5×15 cm) on 50 g of silica gel and N-myristoyl-D-alanine 3.6 g was obtained.

Aufarbeitung

  1. customThe solution reacted
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. customThe oily residue obtained
  5. customwas purified by column chromatography (column: 2.5×15 cm) on 50 g of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7374bf30b50542da84bc57442649a055
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112863

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