Boron Trichloride → HCID 53799376, compound

HRID 744172Notes

Reaction equation

HRID 744172 reaction equation
C([O:8][C@H:9]1[C@@H:13]([O:14]CC2C=CC=CC=2)[C@H:12]([CH2:22][O:23]CC2C=CC=CC=2)[O:11][C@H:10]1[N:31]1[CH:38]=[C:37]([F:39])[C:35](=[O:36])[NH:34][C:32]1=[O:33])C1C=CC=CC=1.B(Cl)(Cl)Cl.C(Cl)Cl.CO>C(Cl)Cl.O>[C@@H:10]1([N:31]2[CH:38]=[C:37]([F:39])[C:35](=[O:36])[NH:34][C:32]2=[O:33])[O:11][C@@H:12]([CH2:22][OH:23])[C@H:13]([OH:14])[C@@H:9]1[OH:8]

Participants

6

Reactant 3

HCID 25135Boron TrichlorideHCID 21226129Dichloromethane methanolHCID 53778230HCID 53778230, compound

Product 1

HCID 53799376HCID 53799376, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 24 (1.0 g, 1.87 mmol) in CH2Cl2 (50 ml), at -78° C. under nitrogen atmosphere, 1M solution of BCl3 (20 ml, 20.57 mmol) was added dropwise. The reaction mixture was stirred at -78° C. for four hours, a 1:1 mixture of CH2Cl2 /MeOH (50 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 (25 ml) 5 times. The residue obtained was dissolved in water and washed with CHCl3 (2×50 ml). The water layer was evaporated to give a white solid which was crystallized from EtOH/ether to give the pure 25 (0.41 g, 83%) as white crystals: m.p. 150° C.

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 (2×50 ml)
  6. customThe water layer was evaporated
  7. customto give a white solid which
  8. customwas crystallized from EtOH/ether

Sources & evidence

ORD record
ord-37c105057193405e8c6dc79cf2bbb696
Source dataset
uspto-grants-1996_09
Patent number
US05559101

Reaction notes

Loading…