Sodium Hydroxide → HCID 178467362, compound

HRID 1099472Notes

Reaction equation

HRID 1099472 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]([C:26]4[N:30]=[N:29][NH:28][N:27]=4)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:31]([O:33]C)=[O:32])[N:5]=1.[OH-].[Na+]>>[CH3:1][CH2:2][O:3][C:4]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[NH:30][N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:11]2[C:10]([C:31]([OH:33])=[O:32])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 15654696Methyl candesartan

Product 1

HCID 178467362HCID 178467362, compound

Conditions

Temperature
70 °C

Procedure

In the second step candesartan methyl ester is added to NaOH solution and is stirred for 1-2 hr at 68-72° C. The solution is cooled and washed twice with dichloromethane and once with toluene. To the aqueous solution is added methanol and the solution pH is adjusted to 7.9±0.5 with conc. HCl. The solution is stirred at 25±5° C. for one hr which is added to water and the pH is adjusted to 3.5±0.3 with conc. HCl. The reaction mixture is diluted with water and cooled to 10° C. or less and the product candesartan formed is washed with acetone and dried.

Workup

  1. temperatureThe solution is cooled
  2. washwashed twice with dichloromethane and once with toluene
  3. additionTo the aqueous solution is added methanol
  4. stirringThe solution is stirred at 25±5° C. for one hr which
  5. additionis added to water
  6. additionThe reaction mixture is diluted with water
  7. temperaturecooled to 10° C. or less

Sources & evidence

ORD record
ord-afd5937fe7f24285bbec40b9ac6569a4
Source dataset
uspto-grants-2012_03
Patent number
US08143435B2

Reaction notes

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