Water → Tert-butyl 2-(2-(benzyloxy)-5-(4-hydroxypiperidin-1-yl)benzamido)-4-phenylbenzoate

HRID 454598Notes

Reaction equation

HRID 454598 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O1CCCC1.[CH2:29]([O:36][C:37]1[CH:64]=[CH:63][C:62]([N:65]2[CH2:70][CH2:69][CH:68]([O:71][Si](C(C)(C)C)(C)C)[CH2:67][CH2:66]2)=[CH:61][C:38]=1[C:39]([NH:41][C:42]1[CH:54]=[C:53]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:52]=[CH:51][C:43]=1[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:40])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>C(Cl)(Cl)Cl>[CH2:29]([O:36][C:37]1[CH:64]=[CH:63][C:62]([N:65]2[CH2:70][CH2:69][CH:68]([OH:71])[CH2:67][CH2:66]2)=[CH:61][C:38]=1[C:39]([NH:41][C:42]1[CH:54]=[C:53]([C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:52]=[CH:51][C:43]=1[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[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 tetrahydrofuran2×HCID 66991386Tert-butyl 2-(2-(benzyloxy)-5-(4-(tert-butyldimethylsilyloxy)piperidin-1-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 66990194Tert-butyl 2-(2-(benzyloxy)-5-(4-hydroxypiperidin-1-yl)benzamido)-4-phenylbenzoateYield 86.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 1.0 mol/L tetrabutylammonium fluoride-tetrahydrofuran solution (0.56 mL) was added to a tetrahydrofuran (3.2 mL) solution of the obtained tert-butyl 2-(2-(benzyloxy)-5-(4-(tert-butyldimethylsilyloxy)piperidin-1-yl)benzamido)-4-phenylbenzoate (0.32 g), followed by stirring at room temperature for 1 hour. A 1.0 mol/L tetrabutylammonium fluoride-tetrahydrofuran solution (0.28 mL) was added to the reaction mixture, followed by stirring at room temperature for 4 hours. Water was added to the reaction mixture under ice-cooling, and chloroform was added thereto at room temperature. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 90-40% hexane/ethyl acetate] to obtain 0.23 g of tert-butyl 2-(2-(benzyloxy)-5-(4-hydroxypiperidin-1-yl)benzamido)-4-phenylbenzoate.

Workup

  1. stirringby stirring at room temperature for 4 hours
  2. temperaturecooling
  3. customat room temperature
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [eluent: 90-40% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-9db9ea42787a46809cb36fe03a77b991
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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