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Citric Acid → HCID 178515652, compound

HRID 384111
Notes
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Reaction equation

HRID 384111 reaction equation
Br[CH:2]([CH:8](Br)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:11][N:10]=1)[C:3](OCC)=[O:4].Cl.[OH:32][NH2:33].[OH-].[Na+].CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[O:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]2[O:32][N:33]=[C:3]([OH:4])[CH:2]=2)=[N:10][CH:11]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 311Citric AcidHCID 443297Hydroxyamine hydrochlorideHCID 23721981Sodium hydroxide methanolHCID 86641941Ethyl 2,3-dibromo-3-(5-((2-phenoxybenzyl)oxy)-2-pyridinyl)propanoate

Product 1

HCID 178515652HCID 178515652, compound

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2,3-dibromo-3-(5-((2-phenoxybenzyl)oxy)-2-pyridinyl)propanoate (159.3 mg) in tetrahydrofuran (1 ml), 32 mg of hydroxyamine hydrochloride, 0.6 ml of 2.5N sodium hydroxide/methanol solution and 0.078 ml of water were added, and the reaction solution was stirred at room temperature for 2 hours and then heated to reflux overnight. The reaction solution was cooled, then diluted with water, acidified with 10% aqueous citric acid, then extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid). The solvent of the resultant fraction was distilled off under reduced pressure, and then purification by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., chloroform/methanol (9:1)) was carried out to afford the title compound as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureThe reaction solution was cooled
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue obtained
  8. customwas purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid)
  9. distillationThe solvent of the resultant fraction was distilled off under reduced pressure
  10. custompurification by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., chloroform/methanol (9:1))

Sources & evidence

ORD record
ord-112f29fe81dd45acbbafa00569fa008b
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367708B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes