Phosphoric Acid → HCID 69135096, compound

HRID 969508Notes

Reaction equation

HRID 969508 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[C:22]([CH2:23][CH:24](O)[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:21]([OH:33])[C:8]2[N:9]=[C:10]([CH3:20])[N:11](COCC[Si](C)(C)C)[C:7]=2[CH:6]=1)=[O:4].P(=O)(O)(O)O.[OH-].[Na+]>O>[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[C:22]2[CH2:23][CH2:24][CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:33][C:21]=2[C:8]2[N:9]=[C:10]([CH3:20])[NH:11][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 69135076HCID 69135076, compound

Product 1

HCID 69135096HCID 69135096, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 0.69 g (1.4 mmol) 7-hydroxy-6-(2-hydroxy-3-phenyl-propyl)-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic acid dimethylamide and 7 ml phosphoric acid (85%) was heated at 80° C. for 1 h. After cooling to room temperature, the reaction mixture was poured into water and neutralized with 6N sodium hydroxide solution. The precipitate was filtered off and purified by column chromatography on silica gel (dichloromethane/methanol=10:1) to afford 0.34 g (72%) of the title compound as a yellow foam.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitate was filtered off
  3. custompurified by column chromatography on silica gel (dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-12cdb5fb6a4e46389cfe9b23f801d8f1
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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