Boron Trichloride → HCID 131726588, compound

HRID 915868Notes

Reaction equation

HRID 915868 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-fe55685e66504a40ac8085474d4425d1
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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