Lithium Hydroxide → 4-(1-(4-chloro-2-methoxyphenyl)-3-(hydroxymethyl)-1H-pyrrol-2-yl)-3-methylbenzamide

HRID 238409Notes

Reaction equation

HRID 238409 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[O:29][CH3:30])[CH:12]=[CH:13][C:14]=2CCC(OCC)=O)=[C:6]([CH3:31])[CH:5]=1)(=[O:3])[NH2:2].[Li+].[OH-].C[CH2:35][O:36]C(C)=O>CO>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([N:11]2[CH:12]=[CH:13][C:14]([CH2:35][OH:36])=[C:10]2[C:7]2[CH:8]=[CH:9][C:4]([C:1]([NH2:2])=[O:3])=[CH:5][C:6]=2[CH3:31])=[C:23]([O:29][CH3:30])[CH:24]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 67175699ethyl 3-(2-(4-carbamoyl-2-methylphenyl)-1-(4-chloro-2-methoxyphenyl)-1H-pyrrol-3-yl)propanoate

Product 1

HCID 671752774-(1-(4-chloro-2-methoxyphenyl)-3-(hydroxymethyl)-1H-pyrrol-2-yl)-3-methylbenzamideYield 12.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(2-(4-carbamoyl-2-methylphenyl)-1-(4-chloro-2-methoxyphenyl)-1H-pyrrol-3-yl)propanoate (580 mg, 1.3 mmol) in MeOH (5 mL) was added aqueous LiOH solution (2 mol/L, 5 mL), and the reaction mixture was stirred at room temperature for three hours. TLC (PE: EtOAc=1:2) showed that the starting material was consumed. The aqueous layer was washed with EtOAc (10 mL), and acidified by 0.5 N HCl to pH=2. The aqueous layer was extracted with a mixture of EtOAc and MeOH (v/v=10:1, 20 mL×3), and the combined organic layer was washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography and preparative HPLC to afford the titled compound as an off-white solid (68.3 mg, yield: 12.6%).

Workup

  1. customwas consumed
  2. washThe aqueous layer was washed with EtOAc (10 mL)
  3. extractionThe aqueous layer was extracted with a mixture of EtOAc and MeOH (v/v=10:1, 20 mL×3)
  4. washthe combined organic layer was washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography and preparative HPLC

Sources & evidence

ORD record
ord-d1897d7c92764958b4efedf12b20c505
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

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