Sodium Hydroxide → HCID 69135181, compound

HRID 969495Notes

Reaction equation

HRID 969495 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]([C:5]1[C:17]([CH2:18][CH2:19][CH:20](O)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:16]([OH:28])[C:8]2[N:9]=[C:10]([CH3:15])[N:11]([CH2:12][O:13][CH3:14])[C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>>[CH3:1][N:2]([CH3:29])[C:3]([C:5]1[C:17]2[CH2:18][CH2:19][CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:28][C:16]=2[C:8]2[N:9]=[C:10]([CH3:15])[N:11]([CH2:12][O:13][CH3:14])[C:7]=2[CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 691351367-hydroxy-6-(3-hydroxy-3-phenyl-propyl)-3-methoxymethyl-2-methyl-3H-benzoimidazole-5-carboxylic acid dimethylamide

Product 1

HCID 69135181HCID 69135181, compoundYield 59%

Conditions

Temperature
80 °C

Procedure

A suspension of 0.20 g (0.6 mmol) 7-hydroxy-6-(3-hydroxy-3-phenyl-propyl)-3-methoxymethyl-2-methyl-3H-benzoimidazole-5-carboxylic acid dimethylamide in 2 ml 85% ortho-phosphorlc acid was heated to 80° C. After 90 min stirring, the reaction was cooled to room temperature, poured into ice/water and neutralized with 10M sodium hydroxide. The water layer was extracted with dichloromethane, the organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was crystallized from ethyl acetate/petroleum ether to afford 130 mg (59%) of the title compound as a beige powder. m.p. 213°-215° C.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionThe water layer was extracted with dichloromethane
  3. dry with materialthe organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-f4f270c0773642ec8dd92bc3c6ce4d6b
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

Loading…