Hydrochloric Acid → N-(4-hydroxymethyl-3-methoxyphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide

HRID 537619Notes

Reaction equation

HRID 537619 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]([CH:16]2[CH2:21][CH:20]([O: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][CH2:39][CH3:40])[CH:19]([O: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][CH2:58][CH3:59])[CH:18]([O: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][CH2:77][CH3:78])[CH2:17]2)=[O:15])[CH:6]=[CH:7][C:8]=1[C:9](OC)=[O:10].CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.Cl>C1COCC1>[OH:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([NH:13][C:14]([CH:16]2[CH2:21][CH:20]([O: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][CH2:39][CH3:40])[CH:19]([O: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][CH2:58][CH3:59])[CH:18]([O: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][CH2:77][CH3:78])[CH2:17]2)=[O:15])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 87324917N-(3-methoxy-4-methoxycarbonylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamideHCID 131729488DIBAL toluene

Product 1

HCID 53257321N-(4-hydroxymethyl-3-methoxyphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3-Methoxy-4-methoxycarbonylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide (70 mg, 0.06 mmol) was dissolved in dehydrated THF (1 ml), 1M DIBAL/toluene (0.2 ml, 0.012 mmol) was added dropwise, and the mixture was stirred for 5 hr. After completion of the reaction, 1N hydrochloric acid was added to quench the reaction, and the mixture was extracted with chloroform (5 ml) and washed with 1N hydrochloric acid (3 ml). The solvent was evaporated and the residue was precipitated with methanol (10 ml) and slurry-washed with acetonitrile (5 ml) and 1N hydrochloric acid (5 ml) to give N-(4-hydroxymethyl-3-methoxyphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide (60 mg, 0.06 mmol, yield 100%).

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with chloroform (5 ml)
  5. washwashed with 1N hydrochloric acid (3 ml)
  6. customThe solvent was evaporated
  7. customthe residue was precipitated with methanol (10 ml)
  8. washslurry-washed with acetonitrile (5 ml) and 1N hydrochloric acid (5 ml)

Sources & evidence

ORD record
ord-c09acbcc1ebd44e6bffff39155bb55ad
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

Loading…