Sodium Hydroxide → AM-103

HRID 2366099Notes

Reaction equation

HRID 2366099 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[N:29][CH:30]=3)=[CH:21][CH:20]=1)[C:13]([CH2:33][C:34]([CH3:39])([CH3:38])[C:35]([OH:37])=[O:36])=[C:12]2[S:40][C:41]([CH3:44])([CH3:43])[CH3:42].[OH-].[Na+:46]>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[N:29][CH:30]=3)=[CH:23][CH:24]=1)[C:13]([CH2:33][C:34]([CH3:39])([CH3:38])[C:35]([O-:37])=[O:36])=[C:12]2[S:40][C:41]([CH3:44])([CH3:43])[CH3:42].[Na+:46]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 16224456AM-103 free acid

Product 1

HCID 59248882AM-103Yield 100.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[5-(Pyrid-2-ylmethoxy)-3-(2-methyl-2-propylthio)-1-[4-(2-methoxypyrid-5-yl)benzyl]indol-2-yl]-2,2-dimethylpropionic acid (444 g, 0.729 mol) was added to a reactor containing 2.1 L of EtOH and stirred. A NaOH solution (29 g in 218 mL of water; 1.00 equivalents) was added to the reactor and stirred at ambient temperature for about 30 minutes. The reaction was concentrated under vacuum at a temperature of about 40 to about 50° C. under a reduced pressure of about 10 mm Hg to about 30 mm Hg. The compound was subsequently dried under vacuum at a temperature of between 40 and 45° C. under a reduced pressure of between 5 and 10 mm Hg to afford 460 g of desired product in near quantitative yield. The sodium salt had a detectable amount of palladium less than about 10 ppm.

Workup

  1. stirringstirred at ambient temperature for about 30 minutes
  2. concentrationThe reaction was concentrated under vacuum at a temperature of about 40 to about 50° C. under a reduced pressure of about 10 mm Hg to about 30 mm Hg
  3. customThe compound was subsequently dried under vacuum at a temperature of between 40 and 45° C. under a reduced pressure of between 5 and 10 mm Hg

Sources & evidence

ORD record
ord-3703fc65c8504643a390b27fb5fa20a2
Source dataset
uspto-grants-2014_04
Patent number
US08697730B2

Reaction notes

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