Boron tribromide → HCID 10300766, compound

HRID 1062471Notes

Reaction equation

HRID 1062471 reaction equation
[CH:1]1([NH:4][S:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[C:20]([Cl:21])=[CH:19][C:18]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])=[CH:17][C:16]=3[Cl:30])[CH:11]=[CH:10][C:9]=2[O:31]C)(=[O:7])=[O:6])[CH2:3][CH2:2]1.B(Br)(Br)Br>ClCCl>[CH:1]1([NH:4][S:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[C:16]([Cl:30])=[CH:17][C:18]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])=[CH:19][C:20]=3[Cl:21])[CH:11]=[CH:10][C:9]=2[OH:31])(=[O:6])=[O:7])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22285672HCID 22285672, compound

Product 1

HCID 10300766HCID 10300766, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound of Step F (16 mg, 0.032 mmol) in dichloromethane (0.5 ml) at 0° C. was added boron tribromide (1M in dichloromethane, 0.06 ml, 0.06 mmol). The reaction mixture was stirred at room temperature for one hour, then quenched by addition of 1N HCl (5 ml). The resulting solution was extracted with dichloromethane (3×5 ml). The combined extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by preparative TLC (7% methanol in dichloromethane) to afford the title compound (11 mg, 68% yield) as a white solid. MS (APCI−) Calc: 502.0, Found: 501.2 (M−1).

Workup

  1. customquenched by addition of 1N HCl (5 ml)
  2. extractionThe resulting solution was extracted with dichloromethane (3×5 ml)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f0666bfbbb294534859be50147e58173
Source dataset
uspto-grants-2005_11
Patent number
US06960604B2

Reaction notes

Loading…