Potassium Carbonate → trans-7-Bromo-1-neopentyl-5-(2-pyridyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

HRID 1803Notes

Reaction equation

HRID 1803 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:10](=[O:17])[C@@H:9]([CH2:18][C:19]([O:21]CC)=[O:20])[O:8][C@H:7]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[C:6]=2[CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:10](=[O:17])[C@@H:9]([CH2:18][C:19]([OH:21])=[O:20])[O:8][C@H:7]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[C:6]=2[CH:30]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69946006Ethyl trans-7-bromo-1-neopentyl-5-(2-pyridyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate

Product 1

HCID 69947563trans-7-Bromo-1-neopentyl-5-(2-pyridyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acidYield 69.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml of methanol was dissolved 1.9 g of ethyl trans-7-bromo-1-neopentyl-5-(2-pyridyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate obtained in Example 131. To the solution was added 10 ml of an aqueous solution containing 1.1 g of potassium carbonate. The mixture was heated and refluxed for 30 minutes, and then concentrated under reduced pressure. The concentrate was crystallized by the addition of 30 ml of a hydrochloric acid aqueous solution. The product was collected by filteration and recrystallized from hexane and ethanol to give 1.25 g of trans-7-bromo-1-neopentyl-5-(2-pyridyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid as prisms, m.p.>263° C. (decomp.)

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was crystallized by the addition of 30 ml of a hydrochloric acid aqueous solution
  5. customThe product was collected by filteration
  6. customrecrystallized from hexane and ethanol

Sources & evidence

ORD record
ord-2f947493a0ee4631a9cc6d66588aa9d1
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Reaction notes

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