2-(4-Bromophenyl)-n-tritylethaneamine → 2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-[hydroxy[4-[2-(tritylamino)ethyl]phenyl]methyl]-4-methylphenyl]-D-glucopyranose

HRID 1009866Notes

Reaction equation

HRID 1009866 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C([Li])CCC.[CH2:35]([O:42][C@@H:43]1[C@@H:49]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@H:48]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C@@H:47]([CH2:66][O:67][CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[O:46][C:44]1([C:75]1[CH:80]=[C:79]([CH:81]=[O:82])[C:78]([CH3:83])=[CH:77][C:76]=1[O:84][CH2:85][C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[OH:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O.O1CCCC1.CCCCCC>[CH2:35]([O:42][C@@H:43]1[C@@H:49]([O:50][CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[C@H:48]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C@@H:47]([CH2:66][O:67][CH2:68][C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[O:46][C:44]1([C:75]1[CH:80]=[C:79]([CH:81]([OH:82])[C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:10][C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:6][CH:7]=2)[C:78]([CH3:83])=[CH:77][C:76]=1[O:84][CH2:85][C:86]1[CH:87]=[CH:88][CH:89]=[CH:90][CH:91]=1)[OH:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 3

HCID 673043972-(4-Bromophenyl)-n-tritylethaneamineHCID 86638438HCID 86638438, compoundHCID 178418339Butyllithium

Product 1

HCID 866384412,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-[hydroxy[4-[2-(tritylamino)ethyl]phenyl]methyl]-4-methylphenyl]-D-glucopyranoseYield 64.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a tetrahydrofuran solution (3 mL) of 2-(4-bromophenyl)-N-tritylethaneamine (0.814 g, 1.84 mmol) was added dropwise under nitrogen atmosphere at −78° C. a 2.66 M hexane solution of n-butyllithium (0.69 mL, 1.84 mmol), and the mixture was stirred for 30 minutes at the same temperature. Then a tetrahydrofuran solution (3 mL) of 2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-formyl-4-methylphenyl]-D-glucopyranose (0.670 g, 0.876 mmol) was added dropwise, and the mixture was stirred for 30 minutes at the same temperature. To the reaction solution was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with NH type silica gel column chromatography (chloroform) to obtain the title compound (0.634 g, 64%) as a yellow oily compound.

Workup

  1. stirringthe mixture was stirred for 30 minutes at the same temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe solvent was evaporated under reduced pressure
  6. customThus obtained residue was purified with NH type silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-4a82470995c24e83b3cd9b9b0cb60d76
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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