Acetic Acid → HCID 58508852, compound

HRID 454715Notes

Reaction equation

HRID 454715 reaction equation
C=O.[C:3](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:21][C:22]1[CH:49]=[CH:48][C:47]([CH:50]2[CH2:55][CH2:54][CH2:53][CH2:52][NH:51]2)=[CH:46][C:23]=1[C:24]([NH:26][C:27]1[CH:39]=[C:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:25]>C(Cl)Cl>[OH:21][C:22]1[CH:49]=[CH:48][C:47]([CH:50]2[CH2:55][CH2:54][CH2:53][CH2:52][N:51]2[CH3:3])=[CH:46][C:23]=1[C:24]([NH:26][C:27]1[CH:39]=[C:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58508516HCID 58508516, compound

Product 1

HCID 58508852HCID 58508852, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 37% aqueous solution of formaldehyde (8.2 μL), acetic acid (9.7 μL), and sodium triacetoxyborohydride (0.045 g) were sequentially added to a methylene chloride (1.5 mL) solution of the obtained tert-butyl 2-(2-hydroxy-5-(piperidin-2-yl)benzamido)-4-phenylbenzoate (0.040 g), followed by stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and chloroform was added thereto. The insoluble substance was removed by filtration, and then 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 magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol] to obtain 0.040 g of tert-butyl 2-(2-hydroxy-5-(1-methylpiperidin-2-yl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and chloroform
  2. additionwas added
  3. customThe insoluble substance was removed by filtration
  4. additiona saturated aqueous solution of sodium bicarbonate was added
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol]

Sources & evidence

ORD record
ord-fe08849bdff5404dbc456f97e61e4df2
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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