Sodium Hydroxide → HCID 59145253, compound

HRID 2389378Notes

Reaction equation

HRID 2389378 reaction equation
[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:32])[N:12]([CH2:14]/[CH:15]=[CH:16]/[C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][N:21]4[CH2:26][C:27]([O:29]CC)=[O:28])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:32])[N:12]([CH2:14]/[CH:15]=[CH:16]/[C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][N:21]4[CH2:26][C:27]([OH:29])=[O:28])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86637916HCID 86637916, compound

Product 1

HCID 59145253HCID 59145253, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (4-{(1E)-3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]-1-propen-1-yl}-1H-indol-1-yl)acetate (70 mg) in MeOH (1.5 mL) was added 1M NaOH aqueous solution (0.2 mL) at ambient temperature. The reaction mixture was stirred at the same temperature for 5 hours. The reaction was quenched with 1M HCl aqueous solution (0.2 mL). The mixture was extracted with EtOAc and washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-97:3) to give (4-{(1E)-3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]-1-propen-1-yl}-1H-indol-1-yl)acetic acid.

Workup

  1. customThe reaction was quenched with 1M HCl aqueous solution (0.2 mL)
  2. extractionThe mixture was extracted with EtOAc
  3. washwashed successively with water and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-97:3)

Sources & evidence

ORD record
ord-895735d1053a4db3a28116baf1d8d197
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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