Sodium Hydroxide → HCID 19853902, compound

HRID 1650382Notes

Reaction equation

HRID 1650382 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:8][CH2:7][CH2:6][C:5]2[C:9]([NH:17]C(=O)C)=[CH:10][CH:11]=[C:12]([C:13]([O:15]C)=[O:14])[C:4]=2[O:3]1.[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:21])[CH2:8][CH2:7][CH2:6][C:5]2[C:9]([NH2:17])=[CH:10][CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19853911HCID 19853911, compound

Product 1

HCID 19853902HCID 19853902, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.5 g (19.0 mmol) of methyl 2,2-dimethyl-6-acetylamino-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylate in 10 ml of methanol is added 10 ml of a 10% aqueous sodium 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 2,2-dimethyl-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-34071375b2744cba8609f875409d47e4
Source dataset
uspto-grants-1990_05
Patent number
US04924010

Reaction notes

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