Acetic Acid → HCID 66990507, compound

HRID 454635Notes

Reaction equation

HRID 454635 reaction equation
[OH-].[Na+].C([O:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[C:13]([CH:36]=1)[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:15])(=O)C.C(O)(=O)C>CO.O1CCOCC1>[CH2:38]([O:37][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][OH:6])=[CH:36][C:13]=1[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:15])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 66990334HCID 66990334, compound

Product 1

HCID 66990507HCID 66990507, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2.0 mol/L aqueous solution of sodium hydroxide (0.37 mL) was added to a solution mixture of tert-butyl 2-(5-(2-acetoxyethyl)-2-(benzyloxy)benzamido)-4-phenylbenzoate (0.38 g) in methanol (1.9 mL) and dioxane (1.9 mL), followed by stirring at room temperature for 2 hours. Acetic acid (0.012 mL) was added to the reaction mixture. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue. 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 0.35 g of tert-butyl 2-(2-(benzyloxy)-5-(2-hydroxyethyl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiona saturated aqueous solution of sodium bicarbonate and ethyl acetate were 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-1f7c6cebd1304a2e807fa700f449c785
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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