Hydrochloric Acid → HCID 58508776, compound

HRID 454618Notes

Reaction equation

HRID 454618 reaction equation
O1CCOCC1.Cl.O1[C:12]2([CH2:17][CH2:16][N:15]([C:18]3[CH:19]=[CH:20][C:21]([OH:46])=[C:22]([CH:45]=3)[C:23]([NH:25][C:26]3[CH:38]=[C:37]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:36]=[CH:35][C:27]=3[C:28]([O:30]C(C)(C)C)=[O:29])=[O:24])[CH2:14][CH2:13]2)[O:11]CC1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[OH:46][C:21]1[CH:20]=[CH:19][C:18]([N:15]2[CH2:16][CH2:17][C:12](=[O:11])[CH2:13][CH2:14]2)=[CH:45][C:22]=1[C:23]([NH:25][C:26]1[CH:38]=[C:37]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:36]=[CH:35][C:27]=1[C:28]([OH:30])=[O:29])=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 58508925HCID 58508925, compound

Product 1

HCID 58508776HCID 58508776, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dioxane (1.0 mL) and 6 mol/L hydrochloric acid (1.0 mL) were added to the obtained tert-butyl 2-(5-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)-2-hydroxybenzamido)-4-phenylbenzoate (0.070 g), followed by heating to reflux for 25 minutes. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto, followed by adjusting the pH to 5.2 with a saturated aqueous solution of sodium bicarbonate. 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 [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: chloroform] to obtain 0.026 g of 2-(2-hydroxy-5-(4-oxopiperidin-1-yl)benzamido)-4-phenylbenzoic acid as a yellow solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 25 minutes
  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
  7. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: chloroform]

Sources & evidence

ORD record
ord-fd77414e8af6479eb9165076f36da269
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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