Water → HCID 54934704, compound

HRID 555280Notes

Reaction equation

HRID 555280 reaction equation
C[O:2][C:3]([C:5]1[CH:19]=[CH:18][C:8]2[N:9]([CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-].O>CO>[CH3:17][S:14]([CH2:13][CH2:12][N:9]1[C:8]2[CH:18]=[CH:19][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[N:11]=[CH:10]1)(=[O:15])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66986996HCID 66986996, compound

Product 1

HCID 54934704HCID 54934704, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-methanesulfonylethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester (0.2 g, 7.09 mmol) in methanol was added LiOH (50 mg) followed by water (1 mL). The reaction mixture was allowed to stir at room temp for 2 h. it was then concentrated to remove methanol and the aqueous layer was acidified with citric acid. The precipitated product was filtered to give 1-(2-Methanesulfonyl-ethyl)-1H-benzoimidazole-5-carboxylic acid (90%). MS-ESI m/z 269 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 12.6 (br, 1H), 8.4 (s, 1H), 8.2 (s, 1H), 7.9 (d, 1H), 7.8 (d, 1H), 4.8 (t, 2H), 3.8 (t, 2H), 3.0 (s, 3H).

Workup

  1. concentrationwas then concentrated
  2. customto remove methanol
  3. filtrationThe precipitated product was filtered

Sources & evidence

ORD record
ord-570588465d5042efadbb41c37e1288bc
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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