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

HRID 1427109Notes

Reaction equation

HRID 1427109 reaction equation
[CH3:1][C:2]1[C:10]([NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]3)[CH:16]=[CH:15][C:14]=2[CH3:26])=[C:9]([CH3:28])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[BH4-].[Na+]>CO>[OH:25][CH:22]1[CH2:23][CH2:24][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:2]([CH3:1])=[C:3]([CH:7]=[CH:8][C:9]=2[CH3:28])[C:4]([OH:6])=[O:5])=[O:27])[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 867073402,4-Dimethyl-3-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoic acid

Product 1

HCID 867073413-[[5-(4-Hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoic acidYield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,4-dimethyl-3-[[2-methyl-5-(4-oxo-1-piperidyl)-benzoyl]amino]benzoic acid (51 mg, 134.05 μmoles) in methanol (1.34 ml) is added sodium tetrahydroborate (10.14 mg, 268.11 μmoles) and the mixture is stirred at ambient temperature. After 1 hour, the mixture is quenched and adjusted to pH7 with saturated solution of NH4Cl and extracted twice with CHCl3 (3 ml):IPA (1 ml). The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The solid is re-dissolved in 3:1 CHCl3:IPA and diluted with HCl to pH2 and extracted with 3:1 CHCl3:IPA. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is taken up in MeOH and filtered through cotton plug. The filtrate is concentrated under reduced pressure followed by dissolution in H2O and lyophilized for 12 hours to afford the title compound as an off-white powder (0.04 g, 81.9%). Mass spectrum (m/z): 383.2 (M+1).

Workup

  1. customthe mixture is quenched
  2. extractionextracted twice with CHCl3 (3 ml)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe solid is re-dissolved in 3:1 CHCl3
  7. additionIPA and diluted with HCl to pH2
  8. extractionextracted with 3:1 CHCl3
  9. dry with materialThe combined organic layers are dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. filtrationfiltered through cotton plug
  13. concentrationThe filtrate is concentrated under reduced pressure
  14. dissolutionfollowed by dissolution in H2O
  15. waitlyophilized for 12 hours

Sources & evidence

ORD record
ord-cceaec98fa764247bdd27210c0ed4f2b
Source dataset
uspto-grants-2015_01
Patent number
US08933098B2

Reaction notes

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