Toluene → N-Fmoc-di(4-docosoxyphenyl)methylamine

HRID 1754820Notes

Reaction equation

HRID 1754820 reaction equation
C(O[C:24]1[CH:60]=[CH:59][C:27]([CH:28](O)[C:29]2[CH:34]=[CH:33][C:32]([O: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][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])=[CH:31][CH:30]=2)=[CH:26][CH:25]=1)CCCCCCCCCCCCCCCCCCCCC.[C:61]([NH2:78])([O:63][CH2:64][CH:65]1[C:77]2[C:72](=[CH:73][CH:74]=[CH:75][CH:76]=2)[C:71]2[C:66]1=[CH:67][CH:68]=[CH:69][CH:70]=2)=[O:62].[CH3:79]S(O)(=O)=O.[CH:84](O)([C:91]1[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1)[C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1.[C:98](=[O:101])([O-])O.[Na+].[C:103]1([CH3:109])[CH:108]=[CH:107][CH:106]=[CH:105][CH:104]=1>>[C:61]([NH:78][CH:28]([C:29]1[CH:30]=[CH:31][C:32]([O: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][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])=[CH:33][CH:34]=1)[C:27]1[CH:59]=[CH:60][C:24]([O:101][CH2:98][CH2:79][CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH2:103][CH2:109][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:91][CH2:84][CH2:85][CH2:90][CH2:89][CH2:88][CH2:87][CH3:86])=[CH:25][CH:26]=1)([O:63][CH2:64][CH:65]1[C:77]2[C:72](=[CH:73][CH:74]=[CH:75][CH:76]=2)[C:71]2[C:66]1=[CH:67][CH:68]=[CH:69][CH:70]=2)=[O:62]

Participants

7

Reactant 6

HCID 1140TolueneHCID 6395Methanesulfonic AcidHCID 7037BenzhydrolHCID 516892Sodium BicarbonateHCID 7363019-Fluorenylmethyl carbamateHCID 469361424,4'-Didocosoxybenzhydrol

Product 1

HCID 86646195N-Fmoc-di(4-docosoxyphenyl)methylamineYield 60%

Conditions

Temperature
100 °C

Procedure

To 4,4′-didocosoxybenzhydrol (713 mg, 856 μmol) were added toluene (15 ml), Fmoc-NH2 (246 mg, 1.03 mmol) and methanesulfonic acid (8.3 μl, 128 μmol), and the mixture was stirred at 100° C. for 3 hr. After confirmation of disappearance of a benzhydrol type anchor, the mixture was cooled to room temperature. 2.5% Aqueous sodium hydrogen carbonate (10 ml) was 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-di(4-docosoxyphenyl)methylamine (540 mg, 512 μmol, yield 60%).

Workup

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

Sources & evidence

ORD record
ord-0a0723aaf2904560bba542791cd066a1
Source dataset
uspto-grants-2015_10
Patent number
US09169187B2

Reaction notes

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