Boron Trichloride → HCID 131726590, compound

HRID 915870Notes

Reaction equation

HRID 915870 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[CH2:36][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[CH2:36][NH:37][N:38]=[CH:39][C:30]([C:31]=32)=[N:29]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 131726591HCID 131726591, compound

Product 1

HCID 131726590HCID 131726590, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of compound 4.5 (68.0 mg, 0.1 mmol) in CH2Cl2 (10 mL) at −78° C. was added 1.0 M solution of BCl3 in CH2Cl2 (1.07 mmol) dropwise via syringe. The mixture was stirred at −78° C. for 1.5 h, then for 3 hr at −35° C. to −40° C. The reaction was quenched by adding MeOH (6.0 mL), the solvents were evaporated and the resulting residue was purified by flash column chromatography over silica gel using 6-7% MeOH in CH2Cl2 as eluent to give title compound 4.6 (31.8 mg) as a white foam.

Workup

  1. waitfor 3 hr at −35° C. to −40° C
  2. customThe reaction was quenched
  3. additionby adding MeOH (6.0 mL)
  4. customthe solvents were evaporated
  5. customthe resulting residue was purified by flash column chromatography over silica gel using 6-7% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-c67c490a856b4f35912c08d0b0d8afb0
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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