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Dodecylamine → n-Dodecyl amide

HRID 333504
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333504
[CH3:1][C@@:2]12[CH:11]3[CH2:12][CH:13]=[C:14]4[C@@H:19]5[CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH2:23][C@:18]5([C:26]([OH:28])=[O:27])[CH2:17][CH2:16][C@@:15]4([CH3:29])[C@:10]3([CH3:30])[CH2:9][CH2:8][C@H:7]1[C@@:6]([OH:32])([CH3:31])[C@@H:5]([OH:33])[CH2:4][CH2:3]2.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:67]([NH2:79])[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH3:78]>C1COCC1.C(Cl)(Cl)Cl.C1CCCCC1.C(OC(=O)C)C>[CH2:67]([NH-:79])[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH3:78].[CH3:1][C@@:2]12[CH:11]3[CH2:12][CH:13]=[C:14]4[C@@H:19]5[CH2:20][C:21]([CH3:24])([CH3:25])[CH2:22][CH2:23][C@:18]5([C:26]([OH:28])=[O:27])[CH2:17][CH2:16][C@@:15]4([CH3:29])[C@:10]3([CH3:30])[CH2:9][CH2:8][C@H:7]1[C@@:6]([OH:32])([CH3:31])[C@@H:5]([OH:33])[CH2:4][CH2:3]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 13583DodecylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44451366(4aS,6aS,6bR,8aR,9S,10S,12aR,14bS)-9,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Produkt 2

HCID 21259697
n-Dodecyl amide
HCID 44451366(4aS,6aS,6bR,8aR,9S,10S,12aR,14bS)-9,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 21867204Cyclohexane ethylacetateLösungsmittel

Versuchsvorschrift

Gypsogenin (1.30 g, 2.76 mmol) was dissolved in dry THF (40 mL) under argon atmosphere at room temperature. DIEA (1.5 ML, 8.28 mmol) and HBTU (1.30 g, 3.31 mmol) were added to the above solution and reaction mixture was stirred for 1 hr at room temperature to produce an intermediate complex. Dodecylamine (614 mg, 3.31 mmol) was added to the reaction mixture which was further stirred for 48 hours at room temperature. TLC using cyclohexane-ethylacetate (1:1) as mobile phase showed the completion of reaction. The reaction was diluted with chloroform, washed with water, dried over sodium sulfate and concentrated to a solid. Column chromatographic purification of crude product on silica gel G using cyclohexane-ethylacetate (3:1 to 2:1) as mobile phase gave pure dodecylamide derivative of gypsogenin in 65% yield. m.p. 85-87° C.

Aufarbeitung

  1. customto produce an intermediate complex
  2. stirringwas further stirred for 48 hours at room temperature
  3. customthe completion of reaction
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a solid
  7. customColumn chromatographic purification of crude product on silica gel G

Quellen und Nachweise

ORD-Eintrag
ord-e536faa079ac405fa234c525cd0b3a9c
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883170B2

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