Methanesulfonic Acid → N-Fmoc-[phenyl(2,3,4-trioctadecanoxyphenyl)methyl]amine

HRID 1754816Notes

Reaction equation

HRID 1754816 reaction equation
[CH2:1]([O:19][C:20]1[C:33]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[C:32]([O: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][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[CH:31]=[CH:30][C:21]=1[CH:22](O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:72]([NH2:89])([O:74][CH2:75][CH:76]1[C:88]2[C:83](=[CH:84][CH:85]=[CH:86][CH:87]=2)[C:82]2[C:77]1=[CH:78][CH:79]=[CH:80][CH:81]=2)=[O:73].CS(O)(=O)=O.C(O)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:72]([NH:89][CH:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:21]1[CH:30]=[CH:31][C:32]([O: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][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])=[C:33]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:20]=1[O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([O:74][CH2:75][CH:76]1[C:88]2[C:83](=[CH:84][CH:85]=[CH:86][CH:87]=2)[C:82]2[C:77]1=[CH:78][CH:79]=[CH:80][CH:81]=2)=[O:73]

Participants

7

Reactant 5

HCID 6395Methanesulfonic AcidHCID 7037BenzhydrolHCID 516892Sodium BicarbonateHCID 7363019-Fluorenylmethyl carbamateHCID 469360472,3,4-Tris(octadecyloxy)benzhydryl alcohol

Product 1

HCID 59510359N-Fmoc-[phenyl(2,3,4-trioctadecanoxyphenyl)methyl]amineYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
50 °C

Procedure

To 2,3,4-trioctadecanoxybenzhydrol (650 mg, 657 μmol) obtained in Example 1 were added toluene (10 ml) and Fmoc-NH2 (189 mg, 790 μmol), and the mixture was warmed to 50° C. in an oil bath. Methanesulfonic acid (6.4 μl, 99 μmol) was added, and the mixture was heated to 100° C. and stirred for 6 hr. After confirmation of disappearance of a benzhydrol type anchor, the mixture was cooled to room temperature. Toluene (5 ml) and 5% aqueous sodium hydrogen carbonate (10 ml) were added and the mixture was stirred. After partitioning, the organic layer was further washed with water (10 ml×2). The organic layer was evaporated under reduced pressure, and the residue was washed with methanol (10 ml) to give N-Fmoc-[phenyl(2,3,4-trioctadecanoxyphenyl)methyl]amine (788 mg, yield 98%).

Workup

  1. temperaturethe mixture was heated to 100° C.
  2. stirringthe mixture was stirred
  3. customAfter partitioning
  4. washthe organic layer was further washed with water (10 ml×2)
  5. customThe organic layer was evaporated under reduced pressure
  6. washthe residue was washed with methanol (10 ml)

Sources & evidence

ORD record
ord-7c38fc20728849bc9c36bfc37032e12e
Source dataset
uspto-grants-2015_10
Patent number
US09169187B2

Reaction notes

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