Acetic Acid → HCID 58508578, compound

HRID 454720Notes

Reaction equation

HRID 454720 reaction equation
[CH:1](=O)[CH3:2].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:22][C:23]1[CH:50]=[CH:49][C:48]([CH:51]2[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)=[CH:47][C:24]=1[C:25]([NH:27][C:28]1[CH:40]=[C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:38]=[CH:37][C:29]=1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:26]>C(Cl)Cl>[CH2:1]([N:54]1[CH2:53][CH2:52][CH:51]([C:48]2[CH:49]=[CH:50][C:23]([OH:22])=[C:24]([CH:47]=2)[C:25]([NH:27][C:28]2[CH:40]=[C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:38]=[CH:37][C:29]=2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:26])[CH2:56][CH2:55]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177Acetaldehyde2×HCID 5049666Sodium triacetoxyborohydride2×HCID 58508443HCID 58508443, compound

Product 1

HCID 58508578HCID 58508578, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetaldehyde (0.016 mL), acetic acid (0.024 mL), and sodium triacetoxyborohydride (0.11 g) were sequentially added to a methylene chloride (1.0 mL) suspension of tert-butyl 2-(2-hydroxy-5-(piperidin-4-yl)benzamido)-4-phenylbenzoate (0.10 g), followed by stirring at room temperature for 1 hour. Acetaldehyde (0.016 mL) and sodium triacetoxyborohydride (0.11 g) were sequentially added to the reaction mixture, followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and ethyl acetate was added to the residue. After removal of the insoluble substance by filtration, a saturated aqueous solution of sodium bicarbonate was added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.045 g of tert-butyl 2-(5-(1-ethylpiperidin-4-yl)-2-hydroxybenzamido)-4-phenylbenzoate as a light yellow solid.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  3. additionwas added to the residue
  4. customAfter removal of the insoluble substance
  5. filtrationby filtration
  6. additiona saturated aqueous solution of sodium bicarbonate was added
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-c951801a7c65439893cd320d22939b1f
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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