Boron Trichloride → HCID 131721197, compound

HRID 1418826Notes

Reaction equation

HRID 1418826 reaction equation
C([O:8][C@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[CH2:12][O:11][C@H:10]1[N:31]1[CH:38]=[C:37]([F:39])[C:35](=O)[NH:34][C:32]1=[O:33])C1C=CC=CC=1.B(Cl)(Cl)Cl.C(Cl)Cl.C[OH:48]>C(Cl)Cl.O>[C@@H:10]1([N:31]2[C:38](=[O:48])[C:37]([F:39])=[CH:35][NH:34][C:32]2=[O:33])[O:11][CH2:12][C@H:13]([OH:23])[C@H:14]([OH:15])[C@@H:9]1[OH:8]

Participants

6

Reactant 3

HCID 25135Boron TrichlorideHCID 15887178HCID 15887178, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 131721197HCID 131721197, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 17 (from Part D) (2.42 g, 4.54 mmol) in CH2Cl2 (100 ml), at -78° C. under nitrogen atmosphere, 1M solution of BCl3 (50 ml, 49.94 mmol) was added dropwise. The reaction mixture was stirred at -78° C. for 4 h and 1:1 mixture of CH2Cl2 /MeOH (100 ml) was added and the reaction mixture was brought to room temperature and the solvents were evaporated to dryness. The residue was coevaporated with MeOH (50 ml) 5 times. The residue obtained was dissolved in water and washed with CHCl3 (50×2) and CCl4 (50 ml). The water layer was evaporated to give a white solid and which was crystallized from EtOH/ether to give the pure 18 (0.94 g, 79.4%) as white crystals: mp 231° C. dec.

Workup

  1. additionwas added
  2. customwas brought to room temperature
  3. customthe solvents were evaporated to dryness
  4. customThe residue obtained
  5. washwashed with CHCl3 (50×2) and CCl4 (50 ml)
  6. customThe water layer was evaporated
  7. customto give a white solid and which
  8. customwas crystallized from EtOH/ether

Sources & evidence

ORD record
ord-59f911f33f7746acbb4bfd5c4227b01f
Source dataset
uspto-grants-1999_03
Patent number
US05885972

Reaction notes

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