Boron tribromide → HCID 57962136, compound

HRID 542034Notes

Reaction equation

HRID 542034 reaction equation
[Cl:1][C:2]1[C:3]2[NH:4][C:5]3[CH:6]=[C:7]4[C:11](=[C:12]([CH:26]=3)[CH2:13][CH2:14][C:15]3[CH:25]=[C:19]([NH:20][C:21]([N:24]=2)=[N:22][CH:23]=1)[CH:18]=[CH:17][CH:16]=3)[O:10][C:9](=[O:27])[N:8]4[CH2:28][C:29]([O:31]C)=[O:30].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:3]2[NH:4][C:5]3[CH:6]=[C:7]4[C:11](=[C:12]([CH:26]=3)[CH2:13][CH2:14][C:15]3[CH:25]=[C:19]([NH:20][C:21]([N:24]=2)=[N:22][CH:23]=1)[CH:18]=[CH:17][CH:16]=3)[O:10][C:9](=[O:27])[N:8]4[CH2:28][C:29]([OH:31])=[O:30]

Participants

4

Reactant 2

HCID 25134Boron tribromide3×HCID 57962467HCID 57962467, compound

Product 1

HCID 57962136HCID 57962136, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
20 °C

Procedure

A solution of methyl [4-chloro-19-oxo-18-oxa-2,6,8,20,25-pentaazapentacyclo[14.6.1.1(3,7).1(9,13).0(17,21)]pentacosa-1(23),3(25),4,6,9(24),10,12,16,21-nonaen-20-yl]acetate (0.23 g, 0.51 mmol) in dichloromethane (15 mL) at −78° C. was treated with 1 M of boron tribromide in dichloromethane (1.5 mL, 1.5 mmol) and stirred at 20° C. for 16 h. The reaction mixture was cooled to 0° C., treated with additional 1 M of boron tribromide in dichloromethane (1.5 mL, 1.5 mmol), and stirred at 20° C. for 6 h. The reaction mixture was cooled to 0° C., quenched with 0.5 M HCl (10 mL) dropwise, concentrated and filtered. The brown solid that was collected was washed with water and dried. This material was diluted with dichloromethane (20 mL), cooled to 0° C., treated with 1 M of boron tribromide in dichloromethane (1.5 mL, 1.5 mmol), and stirred at 20° C. for 24 h. The reaction mixture was cooled to 0° C., quenched with 0.5 M HCl (10 mL) dropwise, concentrated and filtered. The brown solid that was collected was washed with water and dried to give the desired product (0.15 g, 67%) as a tan solid. LCMS for C21H17ClN5O4 (M+H)+: m/z=438.0.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringstirred at 20° C. for 6 h
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customquenched with 0.5 M HCl (10 mL) dropwise
  5. concentrationconcentrated
  6. filtrationfiltered
  7. customThe brown solid that was collected
  8. washwas washed with water
  9. customdried
  10. additionThis material was diluted with dichloromethane (20 mL)
  11. temperaturecooled to 0° C.
  12. stirringstirred at 20° C. for 24 h
  13. temperatureThe reaction mixture was cooled to 0° C.
  14. customquenched with 0.5 M HCl (10 mL) dropwise
  15. concentrationconcentrated
  16. filtrationfiltered
  17. customThe brown solid that was collected
  18. washwas washed with water
  19. customdried

Sources & evidence

ORD record
ord-e48f2e58f75a4f6ea8db08149fa4016f
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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