Phosphoric Acid → HCID 69135168, compound

HRID 969487Notes

Reaction equation

HRID 969487 reaction equation
P(=O)(O)(O)O.[CH3:6][N:7]([CH3:34])[C:8]([C:10]1[C:22]([CH2:23][CH2:24][CH:25]([OH:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:21](O)[C:13]2[N:14]=[C:15]([CH:18]([CH3:20])[CH3:19])[N:16]([CH3:17])[C:12]=2[CH:11]=1)=[O:9].[OH-].[Na+]>>[CH3:6][N:7]([CH3:34])[C:8]([C:10]1[C:22]2[CH2:23][CH2:24][CH:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:32][C:21]=2[C:13]2[N:14]=[C:15]([CH:18]([CH3:20])[CH3:19])[N:16]([CH3:17])[C:12]=2[CH:11]=1)=[O:9]

Participants

4

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 69135055HCID 69135055, compound

Product 1

HCID 69135168HCID 69135168, compoundYield 40%

Procedure

11.6 ml Phosphoric acid (85%) and 1.2 g (3.0 mmol) 2-isopropyl-7-hydroxy-6-(3-hydroxy-3-phenyl-propyl)-3-methyl-3H-benzoimidazole-5-carboxylic acid dimethylamide were heated at 80° C. for 90 min. After cooling to room temperature the reaction mixture was poured into ice-water, neutralized with 6 N sodium hydroxide solution and extracted with ethyl acetate. The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel (dichloromethane/methanol=50:1) to afford 0.4 g (40%) of the title compound as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layers were dried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-25e6e4d1bc2a4775865164d969558e25
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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