Hydroxide → HCID 14502106, compound

HRID 1722653Notes

Reaction equation

HRID 1722653 reaction equation
C([NH:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[C:8]([C:16]([O:18]C)=[O:17])=[CH:7][CH:6]=1)(=O)C.[OH-]>CO>[NH2:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[C:8]([C:16]([OH:18])=[O:17])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 961HydroxideHCID 14502105HCID 14502105, compound

Product 1

HCID 14502106HCID 14502106, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5 g (19.0 mmol) of methyl 6-acetylamino-2,3,4,5-tetrahydro-1-benzoxepin-9-carboylate in 10 ml of methanol is added 10 ml of a 10% aqueous solution hydroxide solution in a single portion at room temperature. The reaction mixture is heated to reflux and maintained at that temperature for 2 hours. After cooling, methanol is removed in vacuo and the residue is diluted with water. The pH of the solution is adjusted to 7 with 1N HCl and the solution is extracted with CH2Cl2. The combined organic extracts are dried over MgSO4, filtered and concentrated. Flash chromatography (30% EtOAc/hexanes) gives 6-amino-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. temperaturemaintained at that temperature for 2 hours
  4. temperatureAfter cooling
  5. custommethanol is removed in vacuo
  6. additionthe residue is diluted with water
  7. extractionthe solution is extracted with CH2Cl2
  8. dry with materialThe combined organic extracts are dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1ab14faeeb0440e4b1516c9295ca7ae0
Source dataset
uspto-grants-1989_08
Patent number
US04857517

Reaction notes

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