Boron Trichloride → HCID 131726588, compound

HRID 2234785Notes

Reaction equation

HRID 2234785 reaction equation
[CH3:1][C@@:2]1([OH:41])[C@H:6]([O:7]CC2C=CC(Cl)=CC=2Cl)[C@@H:5]([CH2:17][O:18]CC2C=CC(Cl)=CC=2Cl)[O:4][C@H:3]1[N:28]1[CH:40]=[C:32]2[CH2:33][CH2:34][C:35]3[O:36][NH:37][N:38]=[CH:39][C:30]([C:31]=32)=[N:29]1.B(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][C@@:2]1([OH:41])[C@H:6]([OH:7])[C@@H:5]([CH2:17][OH:18])[O:4][C@H:3]1[N:28]1[CH:40]=[C:32]2[CH2:33][CH2:34][C:35]3[O:36][NH:37][N:38]=[CH:39][C:30]([C:31]=32)=[N:29]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 131726589HCID 131726589, compound

Product 1

HCID 131726588HCID 131726588, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of compound 2.8 (128.0 mg, 0.20 mmol) in CH2Cl2 (25 mL) at −78° C., was added a 1.0M solution of BCl3 in CH2Cl2 (2.0 mL, 2.0 mmol) dropwise via syringe. The mixture was stirred at −78° C. for 1.5 h, then at −35° C. to −40° C. for 2.5 hr. The reaction was quenched with MeOH (8.0 ml) and the solvents were evaporated. The resulting crude product was purified by flash column chromatography over silica gel using 5% MeOH in CH2Cl2 as eluent to give the title compound 2.9 (59.2 mg) as a white foam.

Workup

  1. waitat −35° C. to −40° C. for 2.5 hr
  2. customThe reaction was quenched with MeOH (8.0 ml)
  3. customthe solvents were evaporated
  4. customThe resulting crude product was purified by flash column chromatography over silica gel using 5% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-42558ea9ff8142d781fc23ce692dcdfa
Source dataset
uspto-grants-2010_05
Patent number
US07713941B2

Reaction notes

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