Hydrochloric Acid → 3-{2,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoylamino}-propionic acid

HRID 1967048Notes

Reaction equation

HRID 1967048 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][CH2:6][NH:7][C:8](=[O:40])[C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([O:16][C:17]2[C:22]([C:23]([N:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]([CH:35]4[CH2:37][CH2:36]4)[CH2:27][CH2:26]3)=[O:24])=[CH:21][N:20]=[C:19]([CH3:38])[CH:18]=2)=[CH:11][C:10]=1[Cl:39])C.O.O.[OH-].[Li+].Cl>O1CCOCC1.C(OCC)(=O)C>[Cl:39][C:10]1[CH:11]=[C:12]([O:16][C:17]2[C:22]([C:23]([N:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]([CH:35]4[CH2:37][CH2:36]4)[CH2:27][CH2:26]3)=[O:24])=[CH:21][N:20]=[C:19]([CH3:38])[CH:18]=2)[C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:41])=[O:3])=[O:40]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 533114503-{2,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoylamino}-propionic acid ethyl ester

Product 1

HCID 533115343-{2,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoylamino}-propionic acidYield 100%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 83 mg (0.139 mmol) 3-{2,5-dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoylamino}-propionic acid ethyl ester in 2 mL dioxane was added 2 mL water and 7 mg (0.174 mmol) lithium hydroxide monohydrate. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was poured on 20 mL 1N aqueous hydrochloric acid and 20 mL ethyl acetate and the layers were separated. The aqueous layer was extracted with 20 mL ethyl acetate and the organic layers were washed with 30 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum to give the title compound as a light yellow solid (100%). MS (ESI): m/z=569.136 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with 20 mL ethyl acetate
  3. washthe organic layers were washed with 30 mL brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4cc4a9b5579f4393aed42ff3a986673d
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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