1-Methylimidazole → Ethyl 2-octadecanoylamino-3-oxooctadecanoate

HRID 222828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222828
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][NH:6][C:7](=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH3:2].CN1C=CN=C1.[C:33](Cl)(=[O:49])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48].C(N(CCCC)CCCC)CCC>[Ti](Cl)(Cl)(Cl)Cl.O.C(Cl)Cl>[C:7]([NH:6][CH:5]([C:33](=[O:49])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:4]([O:3][CH2:1][CH3:2])=[O:26])(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

8

Edukt 4

HCID 13901-MethylimidazoleHCID 7622TributylamineHCID 8206Palmitoyl chlorideHCID 21445007N-octadecanoylglycine ethyl ester

Produkt 1

HCID 24880587Ethyl 2-octadecanoylamino-3-oxooctadecanoateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24193Titanium TetrachlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel4×

Versuchsvorschrift

A methylene chloride solution (100 ml) of N-octadecanoylglycine ethyl ester (3.70 g, 10 mmol) and N-methylimidazole (985.4 mg, 12 mmol) was cooled to −45° C., and a methylene chloride solution (10 ml) of palmitoyl chloride (2.76 mg, 9.74 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 20 minutes at the same temperature, a methylene chloride solution (10 ml) of titanium tetrachloride (6.81 mg, 35 mmol) and a methylene chloride solution (10 ml) of tributylamine (7.42 g, 40 mmol) were added thereto. The resulting mixture was stirred for 2 hours at −45° C. After 100 ml of water was added thereto and the mixture was heated to room temperature, the organic layer was separated. Further, the water layer was extracted twice with methylene chloride (100 ml), and the organic layers were combined and dried with magnesium sulfate. After the solvent was removed in reduced pressure, the obtained crude product was purified by silica gel chromatography (Kieselgel 60 manufactured by Merck, hexane:ethyl acetate=4:1) to obtain the title compound (3.20 mg, yield: 54%).

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 2 hours at −45° C
  2. customthe organic layer was separated
  3. extractionFurther, the water layer was extracted twice with methylene chloride (100 ml)
  4. dry with materialdried with magnesium sulfate
  5. customAfter the solvent was removed in reduced pressure
  6. customthe obtained crude product
  7. customwas purified by silica gel chromatography (Kieselgel 60 manufactured by Merck, hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-6be9ad4ab88b4d63b73c8d58ff515973
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207370B2

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