Salicylamide → o-[[(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl]oxy]-benzamide

HRID 129068

Reaktionsgleichung

Reaktionsgleichung von HRID 129068
[CH2:1]([C@H:7]1[C@H:10]([CH2:11][C@H:12]([OH:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45]([NH2:54])(=[O:53])[C:46]1[C:47](=[CH:49][CH:50]=[CH:51][CH:52]=1)O.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH2:1]([C@@H:7]1[C:8](=[O:25])[O:9][C@H:10]1[CH2:11][C@@H:12]([O:24][C:52]1[CH:51]=[CH:50][CH:49]=[CH:47][C:46]=1[C:45]([NH2:54])=[O:53])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

6

Edukt 4

HCID 5147SalicylamideHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 104282483-Hexyl-4-((R)-2-hydroxytridecyl)-2-oxetanone, (3S,4S)-

Produkt 1

HCID 54133504o-[[(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl]oxy]-benzamideAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.1 g of (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone, 1.6 g of triphenylphosphine, 0.825 g of salicylamide and 3 g of molecular sieve (4 Å) were treated with 20 ml of THF and cooled to 0° C. Thereupon, 1.4 g of di-t-butyl azodicarboxylate were added. After warming to room temperature and stirring the reaction mixture was concentrated and the residue was partitioned between methanol/water (70:30) and hexane and extracted with hexane. The hexane phase was dried and concentrated and the residue was chromatographed on silica gel with hexane/ethyl acetate (4:1). There were obtained 0.727 g of o-[[(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl]oxy]-benzamide, MS: 474 (M+H)+.

Aufarbeitung

  1. temperatureAfter warming to room temperature
  2. concentrationwas concentrated
  3. customthe residue was partitioned between methanol/water (70:30) and hexane
  4. extractionextracted with hexane
  5. dry with materialThe hexane phase was dried
  6. concentrationconcentrated
  7. customthe residue was chromatographed on silica gel with hexane/ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-5ec19bf755b94c5ca8e7a8d5d56850b2
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466708

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