Boron tribromide → HCID 9888680, compound

HRID 1168085Notes

Reaction equation

HRID 1168085 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:28])[C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[C:19]([CH:25]([CH3:27])[CH3:26])[CH:18]=1)[CH2:5][CH:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12].B(Br)(Br)Br>ClCCl>[Cl:28][C:14]1[CH:13]=[C:4]([CH:3]=[C:2]([Cl:1])[C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH:25]([CH3:26])[CH3:27])[CH:18]=1)[CH2:5][CH:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22285666HCID 22285666, compound

Product 1

HCID 9888680HCID 9888680, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound from Step E (26 mg, 0.058 mmol) in dichloromethane (1 ml) at room temperature was added boron tribromide (1M in dichloromethane, 0.12 ml, 0.12 mmol). A tan precipitation was immediately formed. After stirring at room temperature for about 30 minutes, the mixture was quenched with water (5 ml), and extracted with dichloromethane (3×10 ml). The combined extracts were dried, filtered, and concentrated. The residue was purified by preparative TLC (7% methanol in dichloromethane) to afford the title compound (19 mg) as a solid. MS (APCl−) Calc: 425.0, Found: 424.0 (M−1).

Workup

  1. customA tan precipitation
  2. customwas immediately formed
  3. customthe mixture was quenched with water (5 ml)
  4. extractionextracted with dichloromethane (3×10 ml)
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative TLC (7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a803a2ac1d4c4382a1919e9e41927b23
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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