Sodium Hydroxide → HCID 10483547, compound

HRID 1245429Notes

Reaction equation

HRID 1245429 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]([CH2:22][NH:23][CH2:24][C:25]1[CH:26]=[C:27]([C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38]4[CH:47]=[CH:46][CH:45]=[CH:44][C:39]=4[C:40]([O:42]C)=[O:41])=[CH:33][CH:32]=3)[CH:28]=[CH:29][CH:30]=1)=[O:21])[CH:14]=[CH:13]2>O1CCCC1.CO.O.C(OCC)(=O)C>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]([CH2:22][NH:23][CH2:24][C:25]1[CH:26]=[C:27]([C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38]4[CH:47]=[CH:46][CH:45]=[CH:44][C:39]=4[C:40]([OH:42])=[O:41])=[CH:33][CH:32]=3)[CH:28]=[CH:29][CH:30]=1)=[O:21])[CH:14]=[CH:13]2

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 11758351HCID 11758351, compound

Product 1

HCID 10483547HCID 10483547, compoundYield 50.8%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

80 mg (2 mmol) of sodium hydroxide are added to a solution of 0.8 g (1.3 mmol) of methyl 2-[3′-({[6-(2-methoxyethoxymethoxy)naphthalene-2-carbonyl]methylamino}methyl)biphenyl-4-ylamino]benzoate in 8 ml of tetrahydrofuran, 0.8 ml of methanol and a few drops of water. After stirring at room temperature for 8 hours, the reaction medium is diluted with ethyl acetate, washed with aqueous 1N hydrochloric acid solution, extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture and then triturated from heptane. 390 mg (50%) of 2-[3′-({[6-(2-methoxyethoxymethoxy)-naphthalene-2-carbonyl]methylamino}methyl)biphenyl-4-ylamino]benzoic acid are obtained in the form of a yellow powder.

Workup

  1. washwashed with aqueous 1N hydrochloric acid solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 70/30 heptane/ethyl acetate mixture
  9. customtriturated from heptane

Sources & evidence

ORD record
ord-503ff39d259e4ba6aeed4f33e31185ce
Source dataset
uspto-grants-2006_10
Patent number
US07125869B2

Reaction notes

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