Sodium Hydroxide → Tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate

HRID 454619Notes

Reaction equation

HRID 454619 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:8]=[CH:9][C:10]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:11]([CH:34]=1)[C:12]([NH:14][C:15]1[CH:27]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=[CH:24][C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:13])(=O)C>CO.O1CCOCC1>[CH2:36]([O:35][C:10]1[CH:9]=[CH:8][C:7]([OH:6])=[CH:34][C:11]=1[C:12]([NH:14][C:15]1[CH:27]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=[CH:24][C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:13])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66990376Tert-butyl 2-(5-acetoxy-2-(benzyloxy)benzamido)-4-phenylbenzoate

Product 1

HCID 66990772Tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoateYield 97.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2.0 mol/L aqueous solution of sodium hydroxide (1.6 mL) was added to a solution mixture of tert-butyl 2-(5-acetoxy-2-(benzyloxy)benzamido)-4-phenylbenzoate (0.58 g) in methanol (3.0 mL) and dioxane (2.0 mL), followed by stirring at room temperature for 30 minutes. The solvent was evaporated under reduced pressure, and water and chloroform were added to the residue, followed by adjusting the pH to 4.0 with 2.0 mol/L hydrochloric acid. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 0.52 g of tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and chloroform
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4df4b23100ff4496b87a3e91d8a4fc26
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…