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Ethanol → 2-methyl-4-(3-methylindol-2-yl)-2-[(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]butyric acid

HRID 1681743
Notes
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Reaction equation

HRID 1681743 reaction equation
[CH3:1][C:2]1([CH2:17][C:18]2[N:19]=[CH:20][N:21]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:22]=2[CH3:23])[C:15](=[O:16])[N:6]2[C:7]3[C:12]([C:13]([CH3:14])=[C:5]2[CH2:4][CH2:3]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[OH-].[Na+].C([OH:47])C>O1CCOCC1>[CH3:1][C:2]([CH2:17][C:18]1[N:19]=[CH:20][N:21]([C:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:22]=1[CH3:23])([CH2:3][CH2:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH3:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:15]([OH:47])=[O:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 100532708,9-dihydro-7,10-dimethyl-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 104155442-methyl-4-(3-methylindol-2-yl)-2-[(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]butyric acid

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 8,9-dihydro-7,10-dimethyl-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (3.78 g), aqueous 3N sodium hydroxide solution (10 ml), ethanol (10 ml) and dioxane (5 ml) was heated at 90° C. for 30 hours. After evaporation of the solvent, the residue was diluted with water, neutralized with aqueous oxalic acid solution, and extracted three times with chloroform. The chloroform layer was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give 2-methyl-4-(3-methylindol-2-yl)-2-[(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]butyric acid (3.3 g) as an amorphous powder. The product was used in the next reaction without purification.

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue was diluted with water
  3. extractionextracted three times with chloroform
  4. washThe chloroform layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8370d096eb9d462b9b157956e5516ab2
Source dataset
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05173493

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes