Water → Methyl 2-(2-(benzyloxy)-5-(1-(2-hydroxyethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate

HRID 454726Notes

Reaction equation

HRID 454726 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O1CCCC1.[CH2:29]([O:36][C:37]1[CH:61]=[CH:60][C:59]([CH:62]2[CH2:67][CH2:66][N:65]([CH2:68][CH2:69][O:70][Si](C(C)(C)C)(C)C)[CH2:64][CH2:63]2)=[CH:58][C:38]=1[C:39]([NH:41][C:42]1[CH:51]=[C:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:49]=[CH:48][C:43]=1[C:44]([O:46][CH3:47])=[O:45])=[O:40])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>C(OCC)(=O)C>[CH2:29]([O:36][C:37]1[CH:61]=[CH:60][C:59]([CH:62]2[CH2:63][CH2:64][N:65]([CH2:68][CH2:69][OH:70])[CH2:66][CH2:67]2)=[CH:58][C:38]=1[C:39]([NH:41][C:42]1[CH:51]=[C:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:49]=[CH:48][C:43]=1[C:44]([O:46][CH3:47])=[O:45])=[O:40])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11078149TBAF tetrahydrofuranHCID 66990280Methyl 2-(2-(benzyloxy)-5-(1-(2-(tert-butyldimethylsilyloxy)ethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 66991286Methyl 2-(2-(benzyloxy)-5-(1-(2-hydroxyethyl)piperidin-4-yl)benzamido)-4-phenylbenzoateYield 78.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 1.0 mol/L tetrabutylammonium fluoride-tetrahydrofuran solution (0.38 mL) was added to a tetrahydrofuran (1.3 mL) solution of the obtained methyl 2-(2-(benzyloxy)-5-(1-(2-(tert-butyldimethylsilyloxy)ethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate (0.13 g), followed by stirring at room temperature for 4 hours. Under ice-cooling, water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol] to obtain 0.085 g of methyl 2-(2-(benzyloxy)-5-(1-(2-hydroxyethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol]

Sources & evidence

ORD record
ord-0530a2afe7e44490a27e202b87d8243e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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