Lithium hydroxide, monohydrate → 3-(4-tert-Butoxycarbonyl-piperazine-1-carbonyl)-2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-7-carboxylic acid

HRID 1963057Notes

Reaction equation

HRID 1963057 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][N:8]2[C:12]([CH:13]=1)=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[CH3:28])=[C:9]2[C:29]([N:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]1)=[O:30])=[O:4].O.[OH-].[Li+]>O1CCOCC1.O>[C:40]([O:39][C:37]([N:34]1[CH2:33][CH2:32][N:31]([C:29]([C:9]2[N:8]3[C:12]([CH:13]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7]3)=[C:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:10]=2[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[CH3:28])=[O:30])[CH2:36][CH2:35]1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 706639703-(4-tert-Butoxycarbonyl-piperazine-1-carbonyl)-2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-7-carboxylic acid methyl ester

Product 1

HCID 677727443-(4-tert-Butoxycarbonyl-piperazine-1-carbonyl)-2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-7-carboxylic acidYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

The compound of step 5 (0.159 g, 0.27 mmol) was dissolved in 2 ml of dioxane, and a solution of lithium hydroxide hydrate (0.034 g, 0.82 mmol) in 0.8 ml water was added. The solution was stirred at 50° C. overnight. The solvents were then evaporated under reduced pressure, the residue was dissolved in 6 ml of water and acidified to pH 1 with 1 N hydrochloric acid. The product was filtered off, dissolved in EA and the solution washed with brine. The organic phase was dried over sodium sulfate, filtered and evaporated to give 0.139 g of the title compound as a light-brown powder.

Workup

  1. customThe solvents were then evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in 6 ml of water
  3. filtrationThe product was filtered off
  4. dissolutiondissolved in EA
  5. washthe solution washed with brine
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-41e464551c4a4148be75417bf5d1864e
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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