1-Hydroxybenzotriazole → N-(3-methoxy-4-methoxycarbonylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide

HRID 1502548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502548
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.C1C=CC2N(O)N=NC=2C=1.[CH2:24]([O:42][CH:43]1[CH:48]([O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[CH:47]([O:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86])[CH2:46][CH:45]([C:87](O)=[O:88])[CH2:44]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl>[CH3:13][O:12][C:4]1[CH:3]=[C:2]([NH:1][C:87]([CH:45]2[CH2:46][CH:47]([O:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86])[CH:48]([O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[CH:43]([O:42][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:44]2)=[O:88])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 168705Methyl 4-amino-o-anisateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 873243853,4,5-Tris(octadecyloxy)cyclohexylcarboxylic acid

Produkt 1

HCID 87324917N-(3-methoxy-4-methoxycarbonylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamideAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Methyl 4-amino-2-methoxybenzoate (79 mg, 0.44 mmol) was dissolved in chloroform (1 ml), and HOBt (7 mg, 0.05 mmol) and 3,4,5-tris(octadecyloxy)cyclohexylcarboxylic acid (201 mg, 0.22 mmol) were added. EDC.HCl (45 mg, 0.23 mmol) was added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was evaporated, and the residue was precipitated with acetonitrile (10 ml), and then purified by silica gel column chromatography (chloroform/ethyl acetate=10:1) to give N-(3-methoxy-4-methoxycarbonylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide (70 mg, 0.06 mmol, yield 27%).

Aufarbeitung

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. customthe residue was precipitated with acetonitrile (10 ml)
  5. custompurified by silica gel column chromatography (chloroform/ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-62d0add5149f4c43b15c2ec1d9af7abc
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206230B2

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