L-Serine → 2-Methyl Oleoyl-L-Serine

HRID 218122

Reaktionsgleichung

Reaktionsgleichung von HRID 218122
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[CH3:19][CH:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:21](O)=[O:22]>O1CCCC1>[CH3:19][CH:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:21]([NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])=[O:22]

Komponenten

6

Edukt 4

HCID 5951L-SerineHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 99222352-Methyl oleic acid

Produkt 1

HCID 469122122-Methyl Oleoyl-L-Serine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A solution of L-serine (190 mg, 1.8 mmol) in 20 ml. of 0.1 N sodium carbonate and 0.1 N sodium bicarbonate was added to a solution of N-hydroxysuccinimide ester of 2-methyl oleic acid (204.5 mg, 0.5 mmole) in 20 ml tetrahydrofuran. The reaction mixture was stirred overnight at 35° C., evaporated down to 20 ml, and acidified to pH 1 with 1 N HCl. The product was extracted with methylene chloride (2×20 mL), dried (MgSO4), and the solvent evaporated under reduced pressure. The crude material was chromatographed on silica gel (eluting with chloroform:methanol) to give 86 mg (45%) as a yellowish oil 1H NMR (CDCl3) δ 0.912 (t, 3H), 1.129 (d, 3H), 1.288 (s, 20H), 1.611 (m, 2H), 2.018 (m, 4H), 2.323 (m. 1H), 3.787 (dd, 1H), 3.980 (dd, 1H), 4.503 (t, 1H), 5.353 (m, 2H).

Aufarbeitung

  1. customevaporated down to 20 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)

Quellen und Nachweise

ORD-Eintrag
ord-53031352c4a047ffac300995c5a3175e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198327B2

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