Sodium Hydroxide → 3-[[5-[3-(Hydroxymethyl)pyrrolidin-1-yl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoic acid

HRID 239942Notes

Reaction equation

HRID 239942 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:10]C[CH2:8][N:7]([C:11]2[CH:12]=[CH:13][C:14]([CH3:32])=[C:15]([CH:31]=2)[C:16]([NH:18][C:19]2[C:20]([CH3:30])=[C:21]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:22]([O:24]C)=[O:23])=[O:17])[CH2:6]1>CO>[OH:3][CH2:4][CH:5]1[CH2:10][CH2:8][N:7]([C:11]2[CH:12]=[CH:13][C:14]([CH3:32])=[C:15]([CH:31]=2)[C:16]([NH:18][C:19]2[C:20]([CH3:30])=[C:21]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:22]([OH:24])=[O:23])=[O:17])[CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86707321Methyl 3-[[5-[3-(hydroxymethyl)-1-piperidyl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate

Product 1

HCID 867073293-[[5-[3-(Hydroxymethyl)pyrrolidin-1-yl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoic acidYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of aqueous 5N NaOH (5.00 ml) is added to a stirred solution of methyl 3-[[5-[3-(hydroxymethyl)-1-piperidyl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate (0.4 g, 0.975 mmol) in MeOH (5 ml). After 5 hours at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 4 with 1N HCl, and extracted twice with 10% IPA in CH2Cl2. The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the resulting precipitate is triturated with diethyl ether and filtered to afford the title compound as a brown solid (70 mg, 56%). Mass spectrum (m/z): 381.2 (M−1).

Workup

  1. customthe organic solvent is removed under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted twice with 10% IPA in CH2Cl2
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe resulting precipitate is triturated with diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d8d5638d402f4f619107b444c93f7f7c
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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