Ethanol → {(4-Methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methyl}-amine

HRID 1754830Notes

Reaction equation

C(OC(=O)[NH:5][CH:6]([C:78]1[CH:83]=[CH:82][C:81]([O:84][CH3:85])=[CH:80][CH:79]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:15]2[CH2:20][CH:19]([O:21][CH2:22][CH2:23][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][CH3:39])[CH:18]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][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][CH3:58])[CH:17]([O:59][CH2:60][CH2:61][CH2:62][CH2:63][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][CH3:77])[CH2:16]2)=[CH:9][CH:8]=1)C.C(O)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:85][O:84][C:81]1[CH:82]=[CH:83][C:78]([CH:6]([NH2:5])[C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH:15]3[CH2:16][CH:17]([O:59][CH2:60][CH2:61][CH2:62][CH2:63][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][CH3:77])[CH:18]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][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][CH3:58])[CH:19]([O:21][CH2:22][CH2:23][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][CH3:39])[CH2:20]3)=[CH:11][CH:12]=2)=[CH:79][CH:80]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To crude crystals (127 mg) of ethyl{(4-methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methyl}-carbamate were added toluene (2 mL), ethanol (2 mL) and sodium hydroxide (21 mg, 525 μmol) and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was cooled to room temperature, toluene (2 mL) was added, and washed with water (4 mL×3 times) to allow partitioning. The organic layer was evaporated, and the residue was crystallized from acetonitrile (5 mL) to give {(4-methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methyl}-amine (123 mg, 100% vs —OH form).

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with water (4 mL×3 times)
customto allow partitioning
customThe organic layer was evaporated
customthe residue was crystallized from acetonitrile (5 mL)

Sources & evidence

ORD record: ord-530ae4295dcc4fc8b47b4b53ab5e902d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169187B2

Reaction notes

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