Lithium Hydroxide → HCID 59808009, compound

HRID 912589Notes

Reaction equation

HRID 912589 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]([CH3:15])=[CH:13][C:12]([C:16](=[O:28])[NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[C:11]1[CH3:29].[Li+].[OH-]>CO.C1COCC1.O>[CH3:27][S:24]([C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:16]([C:12]2[CH:13]=[C:14]([CH3:15])[N:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:30])=[O:2])[C:11]=2[CH3:29])=[O:28])=[CH:23][CH:22]=1)(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59807952HCID 59807952, compound

Product 1

HCID 59808009HCID 59808009, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-[3-(4-methanesulfonyl-phenylcarbamoyl)-2,5-dimethyl-pyrrol-1-yl]-benzoic acid methyl ester (0.7 g, 1.6 mmol) in MeOH/THF (8 mL: 16 mL) was added LiOH (0.275 g, 6.4 mmol). After stirring 14h at room temperature, the reaction mixture was concentrated in vacuo. The crude reaction mixture was re-dissolved in water and washed with EtOAc. The water layer was separated and then acidified with 1N HCl. The resulting suspension was extracted twice with EtOac. The combined extracts were dried (Na2SO4) and concentrated in vacuo to provide the title compound (0.67 g, 99%) as a white solid. 1H-NMR (DMSO-d6): δ 13.03 (1H, s), 9.81 (1H, s), 8.06 (2H, d, J=9.1), 8.02 (1H, d J=7.8), 7.87 (2H, d, J=8.6), 7.78 (1H, t, J=7.3). 7.68 (1H, t, J=7.8), 7.39 (1H, d, J=7.6), 6.65 (1H, s), 3.20 (3H, s), 2.23 (3H, s), 1.92 (3H, s); MS (ESI): 413 (MH+).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe crude reaction mixture
  3. washwashed with EtOAc
  4. customThe water layer was separated
  5. extractionThe resulting suspension was extracted twice with EtOac
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6589176442e641a3a96872f6b01871b2
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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