Boron Trichloride → HCID 57948705, compound

HRID 555343Notes

Reaction equation

HRID 555343 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[C:23]2[NH:22][C:21]3[C:16](=[CH:17][C:18]([O:24]C)=[CH:19][CH:20]=3)[C:15]=2[CH2:14][CH:13]([CH3:26])[NH:12]1.B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[C:23]2[NH:22][C:21]3[C:16](=[CH:17][C:18]([OH:24])=[CH:19][CH:20]=3)[C:15]=2[CH2:14][CH:13]([CH3:26])[NH:12]1

Participants

4

Reactant 2

HCID 25135Boron Trichloride2×HCID 57948742HCID 57948742, compound

Product 1

HCID 57948705HCID 57948705, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 64 (157 mg, 0.428 mmol) in 12 mL DCM was added boron trichloride (1M in dichloromethane) (2.14 mL, 2.14 mmol) cautiously in an ice bath. Additional aliquots of boron trichloride were added after the three, six and eight hours. After the last addition, the reaction was left to stir at room temperature for 18 hours. Upon completion, the reaction was quenched with sat NaHCO3. The mixture was washed with dichloromethane, followed by EtOAc. The organic layers were combined then dried with sodium sulfate, filtered and concentrated in vacuo. The product was isolated by flash column chromatography with the gradient 1-3% MeOH in dichloromethane to provide 65 (100 mg, 66).

Workup

  1. additionAfter the last addition
  2. waitthe reaction was left
  3. customUpon completion, the reaction was quenched with sat NaHCO3
  4. washThe mixture was washed with dichloromethane
  5. dry with materialThe organic layers were combined then dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was isolated by flash column chromatography with the gradient 1-3% MeOH in dichloromethane

Sources & evidence

ORD record
ord-75585dbd08d24d50b7533d4512d63c65
Source dataset
uspto-grants-2011_11
Patent number
US08053442B2

Reaction notes

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