Boron tribromide → HCID 59423976, compound

HRID 500636Notes

Reaction equation

HRID 500636 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:37]=[CH:36][C:35]([O:38]C)=[CH:34][C:7]=1[O:8][CH:9]1[CH2:12][N:11]([C:13]([CH3:33])([CH3:32])[CH2:14][CH2:15][C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([NH2:19])=[O:18])[CH2:10]1>ClCCl>[Cl:5][C:6]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][C:7]=1[O:8][CH:9]1[CH2:10][N:11]([C:13]([CH3:33])([CH3:32])[CH2:14][CH2:15][C:16]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([NH2:19])=[O:18])[CH2:12]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59423933HCID 59423933, compound

Product 1

HCID 59423976HCID 59423976, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Boron tribromide (1M in dichloromethane, 1.42 mL, 1.42 mmol) was added to an ice-cooled solution of the product of example 117 (70 mg, 0.142 mmol) in dichloromethane (5 mL) and the mixture was stirred at 0° C. for 1 hour. The reaction was then quenched with 0.88 ammonia (20 mL) and the solution stirred at room temperature for 18 hours. The organic layer was separated. The aqueous layer was extracted with dichloromethane (20 mls). The combined organic solution was washed with saturated sodium hydrogen carbonate solution (10 mL) and dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with pentane:ethyl acetate:methanol:0.88 ammonia (90/10/1), 85:15 to 50:50. The resulting gum was dissolved in methanol (5 mls) and 1N hydrochloric acid in diethyl ether (0.5 ml) added. The solution was evaporated and the solid recrystallised from ethyl acetate/methanol to give the title compound hydrochloride salt as a purple solid in 30% yield, 22 mgs.

Workup

  1. customThe reaction was then quenched with 0.88 ammonia (20 mL)
  2. stirringthe solution stirred at room temperature for 18 hours
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with dichloromethane (20 mls)
  5. washThe combined organic solution was washed with saturated sodium hydrogen carbonate solution (10 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by column chromatography on silica gel
  9. washeluting with pentane
  10. dissolutionThe resulting gum was dissolved in methanol (5 mls)
  11. addition1N hydrochloric acid in diethyl ether (0.5 ml) added
  12. customThe solution was evaporated
  13. customthe solid recrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-0421f5273ae94b76a96dfda57b9580dd
Source dataset
uspto-grants-2010_08
Patent number
US07772223B2

Reaction notes

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