L-Serine → N-Oleoyl-L-Serine

HRID 218121

Reaktionsgleichung

Reaktionsgleichung von HRID 218121
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:21][C@H:22]([C:25]([OH:27])=[O:26])[CH2:23][OH:24].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[C:1]([NH:21][C@H:22]([C:25]([OH:27])=[O:26])[CH2:23][OH:24])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

6

Edukt 3

HCID 5951L-SerineHCID 445639Oleic AcidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 44190514N-Oleoyl-L-Serine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of hydroxysuccinimide ester of oleic acid (395 mg, 1 mmole) in tetrahydrofuran (10 ml) was added to a solution of L-serine (105 mg, 1 mmole) and sodium bicarbonate 84 mg, 1 mmole) in water (10 ml). The reaction mixture was let stirring overnight at room temperature, evaporated down to 10 ml, and acidified to pH 1 with 1 N HCl. The product was extracted with methylene chloride (2×20 mL) and dried (MgSO4) and the solvent evaporated under reduced pressure. The crude material was chromatographed on silica gel (eluting with chloroform:methanol) to give 221.7 mg (60%) as a white powder, m.p. 118 C, NMR (CD3OH, ppm): 5.35-5.32 (m, 2H), 4.57-4.36 (m, 1H), 3.90-3.85 (dd, J=12 Hz, 6 Hz, 1H), 3.82-3.78 (dd, J=12Hz, 6 Hz, 1H), 2.29-2.24 (t, 2H), 2.03-1.98 m, 4H), 1.68-1.58 (m, 2H), 1.32-1.29 (m, 22H), 0.91-0.87 (t, 3H). GC-MS (dTMS): 513, 498, 250, 132 m/z; LC-MS(−p): (M-H)+=368 m/z.

Aufarbeitung

  1. customevaporated down to 10 ml
  2. extractionThe product was extracted with methylene chloride (2×20 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude material was chromatographed on silica gel (eluting with chloroform:methanol)
  6. customto give 221.7 mg (60%) as a white powder

Quellen und Nachweise

ORD-Eintrag
ord-f7a2089e17d24e64bf1bbfd3495da5c8
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198327B2

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