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Sodium Iodide → 4-Methoxycarbonylmethoxy-benzoic acid [1-methoxycarbonyl-2-(4-methoxy carbonyl methoxy-phenyl)-ethylcarbamoyl]-methoxycarbonylmethyl ester

HRID 546364
Notes
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Reaction equation

HRID 546364 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:14][C:15]([CH:17]([O:22][C:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:18]([O:20][CH3:21])=[O:19])=[O:16])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[I-].[Na+].P(O)([O-])([O-])=O.[Na+].[Na+]>CC(C)=O>[CH3:13][O:12][C:10]([CH:9]([NH:14][C:15]([CH:17]([O:22][C:23](=[O:31])[C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:28][CH:29]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:16])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:3][CH:4]=1)=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24203Sodium Phosphate, DibasicHCID 671882054-Hydroxy-benzoic acid [2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl carbamoyl]-methoxycarbonylmethyl ester

Product 1

HCID 671894534-Methoxycarbonylmethoxy-benzoic acid [1-methoxycarbonyl-2-(4-methoxy carbonyl methoxy-phenyl)-ethylcarbamoyl]-methoxycarbonylmethyl ester

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

To a mixture of 4-hydroxy-benzoic acid [2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl carbamoyl]-methoxycarbonylmethyl ester 17 (10.7 grams, 24.82 mmol) anhydrous potassium carbonate (17.5 grams, 126.62 mmol), sodium iodide (3 grams, 20.01 mmol), and disodium phosphate (3 grams, 21.13 mmol) in anhydrous acetone (100 mL) is added methyl chloro acetate (7 grams, 64.5 mmol). The mixture is refluxed for 10 hours. Acetone is distilled off, and water (100 mL) is added. Crude 18 is filtered, dried, and can be purified in appropriate solvent.

Workup

  1. temperatureThe mixture is refluxed for 10 hours
  2. distillationAcetone is distilled off
  3. additionwater (100 mL) is added
  4. filtrationCrude 18 is filtered
  5. customdried
  6. customcan be purified in appropriate solvent

Sources & evidence

ORD record
ord-2973e85d6fc043888793a10857ed1a82
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935843B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes