Boron tribromide → HCID 12019734, compound

HRID 1595153Notes

Reaction equation

HRID 1595153 reaction equation
[CH2:1]([NH:5][C:6]([C:8]1[C@:9]2([CH2:25][CH2:24][C@H:23]3[C@@H:14]([CH2:15][CH2:16][C:17]4[CH:18]=[C:19]([O:26]C)[CH:20]=[CH:21][C:22]=43)[C@@H:11]2[CH2:12][CH:13]=1)[CH3:10])=[O:7])[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([NH:5][C:6]([C:8]1[C@:9]2([CH2:25][CH2:24][C@H:23]3[C@@H:14]([CH2:15][CH2:16][C:17]4[CH:18]=[C:19]([OH:26])[CH:20]=[CH:21][C:22]=43)[C@@H:11]2[CH2:12][CH:13]=1)[CH3:10])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12019733HCID 12019733, compound

Product 1

HCID 12019734HCID 12019734, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution comprising 119 mg of compound 9a in 2 ml of anhydrous CH2Cl2 was added 0.64 ml of BBr3 (1M solution in CH2Cl2) at −15° C. under nitrogen atmosphere. The reaction solution was stirred at room temperature for 1.3 hours and quenched by adding methanol and water at 0° C. The organic layer was separated and the aqueous layer was extracted with chloroform (CHCl3). The combined organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was triturated with 2.5 ml of EtOAc and 2.5 ml of hexane, yielding compound 10a (89 mg, 78%).

Workup

  1. customquenched
  2. additionby adding methanol and water at 0° C
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform (CHCl3)
  5. dry with materialThe combined organic layer was dried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with 2.5 ml of EtOAc and 2.5 ml of hexane

Sources & evidence

ORD record
ord-bfaa745ca40545088e3f0e6cf5756f6f
Source dataset
uspto-grants-2001_09
Patent number
US06288050B1

Reaction notes

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