Water → HCID 69410937, compound

HRID 1350340Notes

Reaction equation

HRID 1350340 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][N:6]([C:14](=[O:34])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21](=[O:33])[NH:22][CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.O.O1CCOCC1.[OH-].[Na+]>C(O)C>[O:28]1[C:27]2[CH:31]=[CH:32][C:24]([CH2:23][NH:22][C:21]([C:17]3[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=3)[C:14]([N:6]([CH2:5][C:4]([OH:35])=[O:3])[CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:34])=[O:33])=[CH:25][C:26]=2[O:30][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 69411675HCID 69411675, compound

Product 1

HCID 69410937HCID 69410937, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-benzo[1,3]dioxol-5-ylmethyl-isophthalamic acid (3.0 g, 10 mmol) in methylene chloride was added 1-hydroxy-benzotriazole monohydrate (“HOBt”) (1.35 g, 10 mmol) and ethyl N-benzylglycine (1.94 g, 10 mmol). To this was added 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (“EDAC”) (1.92 g, 10 mmol) and the mix stirred at room temperature for 24 hours. The solution treated with water (150 mL) and the organic phase separated, washed with 10% citric acid (100 mL), saturated sodium bicarbonate (100 mL) and brine (100 mL). The organic phase dried over magnesium sulfate and evaporated at reduced pressure to give ({3-[(1,3-benzodioxol-5-ylmethyl)-carbamoyl]-benzoyl}-benzyl-amino)-acetic acid ethyl ester as a solid, 3.69 g. To a solution of this ester (3.6 g, 7.6 mmol) in a mix of water (15 mL), dioxane (60 mL) and ethanol (20 mL) was added sodium hydroxide (0.72 g, 18 mmol). The mixture stirred at 50° C. for 24 hours. The solution cooled to room temperature and evaporated at reduced pressure free of solvents. The residue was diluted with water (100 mL) and washed with ether (2×50 mL). The ether discarded and the aqueous phase made acidic with 6N HCl. This was extracted with ethyl acetate (2×100 mL). The organic phases washed with brine (100 mL) and dried over magnesium sulfate. The solvent was evaporated at reduced pressure to give the title compound, 3.41 g. Microanalysis (C25H22N2O6.0.3H2O): Calc'd: C=66.45; H=5.05; N=6.20. Found: C=66.25; H=5.15; N=5.99.

Workup

  1. temperatureThe solution cooled to room temperature
  2. customevaporated at reduced pressure free of solvents
  3. additionThe residue was diluted with water (100 mL)
  4. washwashed with ether (2×50 mL)
  5. extractionThis was extracted with ethyl acetate (2×100 mL)
  6. washThe organic phases washed with brine (100 mL)
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-cd6f4d80ba624243a0fe03f00bbbe3c5
Source dataset
uspto-grants-2007_05
Patent number
US07214712B2

Reaction notes

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