Boron tribromide → HCID 70242181, compound

HRID 1531799Notes

Reaction equation

HRID 1531799 reaction equation
[CH2:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][N:11]([C@@H:15]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([O:36]C)[CH:31]=2)[C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][N:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:23]3)=[CH:18][CH:17]=2)[C@@H:10]([CH3:38])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH2:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][N:11]([C@@H:15]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=2)[C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][N:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:23]3)=[CH:18][CH:17]=2)[C@@H:10]([CH3:38])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 70242089HCID 70242089, compound

Product 1

HCID 70242181HCID 70242181, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 105 (0.34 g) in dichloromethane (20 ml ) at —78° C. was added boron tribromide (2.6 ml ). the reaction was allowed to warm to room temperature. After 2 hours, the reaction was quenched with ammoniacal methanol solution and the solvent removed under reduced pressure. The crude material was purified on silica eluting with 80:20:3 dichloromethane:methanol:ammonium hydroxide. The product containing fractions were pooled and the solvent removed under reduced pressure. The solid was purified further using MCI gel chromatography eluting with a solvent gradient of 100:0 to 0:100 water:methanol. The product-containing fractions were concentrated, a small volume of concentrated ammonium hydroxide added and the solution freeze-dried to give the title compound (0.11 g).

Workup

  1. customthe reaction was quenched with ammoniacal methanol solution
  2. customthe solvent removed under reduced pressure
  3. customThe crude material was purified on silica eluting with 80:20:3 dichloromethane
  4. additionThe product containing fractions
  5. customthe solvent removed under reduced pressure
  6. customThe solid was purified further using MCI gel chromatography
  7. washeluting with a solvent gradient of 100:0 to 0:100 water
  8. concentrationThe product-containing fractions were concentrated
  9. additiona small volume of concentrated ammonium hydroxide added
  10. customthe solution freeze-dried

Sources & evidence

ORD record
ord-c531a66790ac4811ad186a62a1c0d07c
Source dataset
uspto-grants-2001_03
Patent number
US06200978B1

Reaction notes

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