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

HRID 2090582Notes

Reaction equation

HRID 2090582 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]

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 180AcetoneSolvent

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-8cb715397e25481d885e95539a209fa1
Source dataset
uspto-grants-2013_05
Patent number
US08436201B2

Reaction notes

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