Carbamic acid, ethyl ester → Ethyl {(4-methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methyl}-carbamate

HRID 1025054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025054
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH:23]([O: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][CH2:41][CH2:42][CH3:43])[CH:22]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[CH:21]([O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])[CH2:20]3)=[CH:13][CH:12]=2)O)=[CH:5][CH:4]=1.[C:82](=[O:87])([O:84][CH2:85][CH3:86])[NH2:83].CS(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([NH:83][C:82](=[O:87])[O:84][CH2:85][CH3:86])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH:23]([O: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][CH2:41][CH2:42][CH3:43])[CH:22]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[CH:21]([O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])[CH2:20]3)=[CH:13][CH:12]=2)=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 5641Carbamic acid, ethyl esterHCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 46935394(4-Methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methanol

Produkt 1

HCID 59510358Ethyl {(4-methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methyl}-carbamateAusbeute 108,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To (4-methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methanol (110 mg, 97.2 μmol) were added toluene (2 mL), ethyl carbamate (17.8 mg, 200 μmol), and methanesulfonic acid (1 μL, 15 μmol), and the mixture was stirred at 110° C. for 2 hours. The reaction mixture was cooled to room temperature, sodium carbonate (5 mg, 47 μmol) was added and the solvent was evaporated. The residue was crystallized from methanol (5 mL) to give ethyl {(4-methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methyl}-carbamate (127 mg, 100%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated
  3. customThe residue was crystallized from methanol (5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-e08ec197fcb6446389f6d0c0d8bcc9e5
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722934B2

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