Sodium borohydride → 4-[[5-(4-Hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoic acid

HRID 1427104Notes

Reaction equation

HRID 1427104 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:28])[C:10]=1[NH:11][C:12](=[O:27])[C:13]1[CH:18]=[C:17]([N:19]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)[CH:16]=[CH:15][C:14]=1[CH3:26])[C:5]([OH:7])=[O:6].[BH4-].[Na+]>CO>[OH:25][CH:22]1[CH2:21][CH2:20][N:19]([C:17]2[CH:16]=[CH:15][C:14]([CH3:26])=[C:13]([CH:18]=2)[C:12]([NH:11][C:10]2[C:9]([CH3:28])=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[CH3:1])=[O:27])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 867073363,5-Dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoic acid

Product 1

HCID 867073374-[[5-(4-Hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoic acidYield 15.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)-benzoyl]amino]benzoic acid (69.5 mg, 182.68 μmoles) in methanol (1.83 ml) is added sodium tetrahydroborate (13.82 mg, 365.36 μmoles) and the resulting mixture is stirred at ambient temperature. After 1 hour, the mixture is quenched with saturated solution of NH4Cl (0.2 ml) and extracted with CHCl3 (3 ml):IPA (1 ml). The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting solid is triturated with H2O (5 ml), filtered, and washed with H2O (5 ml). The residue is purified by reverse phase chromatography (C18) using 20% acetonitrile in H2O with 0.1% formic acid to afford the title compound as a white powder (0.01 g, 15.7%). Mass spectrum (m/z): 383.2 (M+1).

Workup

  1. customthe mixture is quenched with saturated solution of NH4Cl (0.2 ml)
  2. extractionextracted with CHCl3 (3 ml)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid is triturated with H2O (5 ml)
  7. filtrationfiltered
  8. washwashed with H2O (5 ml)
  9. customThe residue is purified by reverse phase chromatography (C18)

Sources & evidence

ORD record
ord-e1a5d685dfd148e2a8828a558af24b6a
Source dataset
uspto-grants-2015_01
Patent number
US08933098B2

Reaction notes

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