Lithium hydroxide, monohydrate → ({2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoyl}-methyl-amino)-acetic acid

HRID 1967012Notes

Reaction equation

HRID 1967012 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][N:5]([C:7](=[O:38])[C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[C:22]([N:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH:34]3[CH2:36][CH2:35]3)[CH2:26][CH2:25]2)=[O:23])=[CH:10][C:9]=1[Cl:37])[CH3:6].O.[OH-].[Li+]>O1CCOCC1.O>[Cl:37][C:9]1[CH:10]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[C:22]([N:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH:34]3[CH2:35][CH2:36]3)[CH2:26][CH2:25]2)=[O:23])[C:12]([Cl:14])=[CH:13][C:8]=1[C:7]([N:5]([CH2:4][C:3]([OH:39])=[O:2])[CH3:6])=[O:38]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53312196({2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoyl}-methyl-amino)-acetic acid methyl ester

Product 1

HCID 53312197({2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoyl}-methyl-amino)-acetic acidYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.057 g (0.10 mmol) ({2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoyl}-methyl-amino)-acetic acid methyl ester (Example 31) in 1 mL dioxane and 1 mL water was added 0.005 g (0.12 mmol) lithium hydroxide monohydrate. After stirring at room temperature for 2 hours, dioxane was removed by evaporation. The pH of the formed yellow solution was adjusted to 1 with 1M aqueous hydrochloric acid. The aqueous solution was saturated with solid sodium chloride and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to give 0.053 g (95%) of the title compound as a yellow solid. MS (ESI): m/z=555.12 [M+H]+.

Workup

  1. customdioxane was removed by evaporation
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-266bc305cea941a988f0ef868f417c68
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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