Sodium Hydroxide → 2-[[(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)carbonyl]amino]acetic acid

HRID 2258440Notes

Reaction equation

HRID 2258440 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[O:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15]([O:17]CC)=[O:16])=[O:12])[C:4]=2[CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[O:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 10570547HCID 10570547, compound

Product 1

HCID 108304472-[[(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)carbonyl]amino]acetic acidYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the product of Example 3 (5.1 g, 14.2 mmol) dissolved in 100 mL of methanol (MeOH) was added 25 mL (25.0 mmol) of 1N sodium hydroxide. (NaOH). This reaction was stirred at room temperature overnight before all solvent was removed under reduced pressure. The residue was dissolved in 250 mL of water and the solution was brought to pH 3 with 1N HCl. The product was extracted from the aqueous phase with 3×250 mL of Et2O. The Et2O layer was then dried (Na2SO4), filtered, and stripped of all solvent under reduced pressure to provide 4.7 g of the title compound after drying in a vacuum oven.

Workup

  1. customwas removed under reduced pressure
  2. dissolutionThe residue was dissolved in 250 mL of water
  3. extractionThe product was extracted from the aqueous phase with 3×250 mL of Et2O
  4. dry with materialThe Et2O layer was then dried (Na2SO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-74e6acb4a2ab44409881aa3291a9b1ff
Source dataset
uspto-grants-1997_08
Patent number
US05661146

Reaction notes

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