Boron tribromide → HCID 25183798, compound

HRID 1925693Notes

Reaction equation

HRID 1925693 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22]C)=[O:21])(=[O:13])=[O:12])=[C:7]([O:24]C)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([OH:22])=[O:21])(=[O:13])=[O:12])=[C:7]([OH:24])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59180379HCID 59180379, compound

Product 1

HCID 25183798HCID 25183798, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 32 (300.0 mg; 0.78 mmol) in dichloromethane (3.9 mL) was added boron tribromide (0.52 mL; 5.47 mL) dropwise. The reaction mixture was stirred at 0° C. then allowed to gradually warm to room temperature. After stirring 4 hours at room temperature, the reaction mixture was cooled to 0° C. again, slowly quenched with methanol; and then diluted with chloroform. The organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was re-dissolved in diethyl ether and washed with aqueous sodium hydroxide (2N). The aqueous layer was acidified to pH˜2 with concentrated hydrochloric acid and extracted with chloroform (3×). The organic extracts were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes and then by preparative HPLC to afford the title compound as a white solid (101 mg).

Workup

  1. temperatureto gradually warm to room temperature
  2. stirringAfter stirring 4 hours at room temperature
  3. temperaturethe reaction mixture was cooled to 0° C. again
  4. customslowly quenched with methanol
  5. additionand then diluted with chloroform
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe crude residue was re-dissolved in diethyl ether
  11. washwashed with aqueous sodium hydroxide (2N)
  12. extractionextracted with chloroform (3×)
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure
  16. customThe crude residue was purified by automated silica gel column chromatography (Biotage®)
  17. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-aea234defb9f42a69a2bc78458bf29c9
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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