Lithium Hydroxide → HCID 59808009, compound

HRID 383759Notes

Reaction equation

HRID 383759 reaction equation
C(OC)(=O)C1C(=CC=CC=1)N.[CH3:12][O:13][C:14](=[O:41])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[C:25]([CH3:26])=[CH:24][C:23]([C:27](=[O:39])[NH:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)=[C:22]1[CH3:40].[Li+].[OH-]>CO.C1COCC1.O>[CH3:12][O:13][C:14](=[O:41])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[C:25]([CH3:26])=[CH:24][C:23]([C:27](=[O:39])[NH:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)=[C:22]1[CH3:40].[CH3:38][S:35]([C:32]1[CH:31]=[CH:30][C:29]([NH:28][C:27]([C:23]2[CH:24]=[C:25]([CH3:26])[N:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14]([OH:41])=[O:13])[C:22]=2[CH3:40])=[O:39])=[CH:34][CH:33]=1)(=[O:37])=[O:36]

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 8635Methyl AnthranilateHCID 59807952HCID 59807952, compound

Product 2

HCID 59807952HCID 59807952, compoundHCID 59808009HCID 59808009, compoundYield 203.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-[3-(4-Methanesulfonyl-phenylcarbamoyl)-2,5-dimethyl-pyrrol-1-yl]-benzoic acid methyl ester was prepared from methyl anthranilate in a manner similar to that described for Examples 1G. 1H-NMR (DMSO-d6): δ 9.58 (1H, s), 7.83 (2H, d, J=8.8), 7.79 (1H, dd J=7.8, 1.5), 7.63 (2H, d, J=7.8), 7.58 (1H, dd, J=7.8, 1.5). 7.48 (1H, td, J=7.6, 1.3), 7.21 (1H, dd, J=7.8, 1.0), 7.15 (1H, s), 6.42 (1H, d, J=1.0), 3.43 (3H, s), 2.96 (3H, s), 1.94 (3H, s), 1.66 (3H, s); MS (ESI): 427 (MH4). 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 14 h 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-65268fa0e3714beeadafa092d6f272d5
Source dataset
uspto-grants-2013_02
Patent number
US08367667B2

Reaction notes

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