Sodium Hydroxide → HCID 19853899, compound

HRID 1723063Notes

Reaction equation

HRID 1723063 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:8][CH2:7][CH2:6][C:5]2[C:9]([NH:18]C(=O)C)=[C:10]([Cl:17])[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([CH3:22])[CH2:8][CH2:7][CH2:6][C:5]2[C:9]([NH2:18])=[C:10]([Cl:17])[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19853896HCID 19853896, compound

Product 1

HCID 19853899HCID 19853899, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.46 g (16.8 mmol) of methyl 2,2-dimethyl-6-acetylamino-7-chloro-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylate in 10 ml of methanol is added 10 ml of a 10% aqueous sodium hyroxide solution in a single portion at room temperature. The solution is heated to reflux and refluxing maintained for 2 hours. After cooling, methanol is removed in vacuo and the residue is diluted with water. The pH of this solution is adjusted to 7 with 1N HCl. The neutral solution is extracted with CH2Cl2 and the combined organic extracts are dried over MgSO4, filtered and concentrated. Flash chromatography (30% EtOAc/hexanes) provides 2,2-dimethyl-6-amino-7-chloro-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux
  3. temperaturerefluxing
  4. temperaturemaintained for 2 hours
  5. temperatureAfter cooling
  6. custommethanol is removed in vacuo
  7. additionthe residue is diluted with water
  8. extractionThe neutral solution is extracted with CH2Cl2
  9. dry with materialthe combined organic extracts are dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-31bb78c1c0bf4d6a99a0d7d73558eb5d
Source dataset
uspto-grants-1989_08
Patent number
US04859683

Reaction notes

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