Trimethylaluminum → Methyl 11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepine-8-carboxylate

HRID 1907776Notes

Reaction equation

HRID 1907776 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([O:21]C)=O)[C:5]([O:7][CH3:8])=[O:6].C[Al](C)C>C(Cl)Cl>[O:21]=[C:19]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[NH:1]1

Participants

4

Reactant 2

HCID 16682925TrimethylaluminumHCID 59737336Methyl 3-amino-4-(2-(methoxycarbonyl)phenoxy)benzoate

Product 1

HCID 59737222Methyl 11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepine-8-carboxylateYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 547 (3.2 g, 10.62 mmol) and AlMe3 (6.37 mL, 12.75 mmol) in DCM (40 mL) was stirred at 45° C. for 16 h and quenched with water. The reaction was diluted with AcOEt, washed with water and 1M HCl. The organic layer was separated, dried with Na2SO4, filtered and concentrated via rotary evaporation. The residue was triturated with AcOEt, filtered, washed with AcOEt and was purified via Isco employing a 0 to 50% AcOEt in hexanes solvent gradient to afford the title compound 548 (1.01 g, 35%) as a white solid.

Workup

  1. customquenched with water
  2. additionThe reaction was diluted with AcOEt
  3. washwashed with water and 1M HCl
  4. customThe organic layer was separated
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated via rotary evaporation
  8. customThe residue was triturated with AcOEt
  9. filtrationfiltered
  10. washwashed with AcOEt
  11. customwas purified via Isco

Sources & evidence

ORD record
ord-d04079e0f1b344e3840c416539c0c3f1
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

Loading…