Boron Trichloride → HCID 53705858, compound

HRID 496544Notes

Reaction equation

HRID 496544 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([B:20]([O:22]C12CC(C1(C)C)CCC2(O)C)[OH:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Cl)(Cl)Cl>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([B:20]([OH:21])[OH:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 131721369HCID 131721369, compound

Product 1

HCID 53705858HCID 53705858, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.93 g. (7 mmol) of (+)-pinanediol-1-benzyloxycarbonylamino-2-phenylethane boronate (IV) in 20 ml of CH2Cl2 at −78° C. is added 24 ml of boron trichloride. The mixture is kept at 20° C. for 2 hrs., then concentrated under vacuum and the residue is washed with ether, treated with methanol, concentrated and dissolved in water. The solution is then neutralized with Dowex 1-x8 ion exchange resin bicarbonate, concentrated and crystallized from THF/water to give (R)-1-benzyloxycarbonylamino-2-phenylethane boronic acid and its anhydride.

Workup

  1. concentration, then concentrated under vacuum
  2. washthe residue is washed with ether
  3. additiontreated with methanol
  4. concentrationconcentrated
  5. dissolutiondissolved in water
  6. concentrationconcentrated
  7. customcrystallized from THF/water

Sources & evidence

ORD record
ord-60eb454674a44133adcf6c2134fcac36
Source dataset
uspto-grants-2005_09
Patent number
US06946272B1

Reaction notes

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