Sodium Carbonate → HCID 67814789, compound

HRID 2401422Notes

Reaction equation

HRID 2401422 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[C:9](=O)[NH:10][C@@H:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:5]=2[O:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:23].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:23][C:9]1[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=2[C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[C@H:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[N:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24819Phosphorus pentachlorideHCID 67951394HCID 67951394, compound

Product 1

HCID 67814789HCID 67814789, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-((4S)-1-methyl-6-oxo-5,6-dihydro-4H-benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetate (0.4754 g, 1.661 mmol) in CH2Cl2 (4 mL) was added phosphorus pentachloride (0.432 g, 2.075 mmol). The reaction mixture was stirred at room temperature for 1 h. To the mixture was added aqueous 10% Na2CO3 and stirred vigorously for 15 min. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4 and concentrated to give yellow foam after drying. The foam was filtered over a plug of silica and eluted with 20% EtOAc:80% Hexanes. The product methyl 2-((4S)-6-chloro-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetate (0.4701 g, 1.543 mmol, 93% yield) was obtained as a white foam. LC/MS m/z 305 [M+H]+.

Workup

  1. stirringstirred vigorously for 15 min
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated
  5. customto give yellow foam
  6. customafter drying
  7. filtrationThe foam was filtered over a plug of silica
  8. washeluted with 20% EtOAc

Sources & evidence

ORD record
ord-b3ce023e2f5040868131c18034766eab
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

Loading…