Boron Trichloride → HCID 135850854, compound

HRID 2216521Notes

Reaction equation

HRID 2216521 reaction equation
B(Cl)(Cl)Cl.C([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[N:22]=[C:21]([C:30]#[C:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:20]=2)=[CH:15][CH:14]=1)C1C=CC=CC=1>C(Cl)Cl>[CH:24]1([N:23]2[C:19]([C:16]3[CH:15]=[CH:14][C:13]([OH:12])=[CH:18][CH:17]=3)=[CH:20][C:21]([C:30]#[C:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:22]2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 11339380HCID 11339380, compound

Product 1

HCID 135850854HCID 135850854, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

A 1M solution of BCl3 in CH2Cl2 (1 ml, 1.00 mmol) was added to a solution of intermediate 7.3 (86 mg, 0.207 mmol) in 2 ml of CH2Cl2 at −50° C., and after being stirred at −50° C. for 15 min, the solution was quenched with MeOH, diluted with EtOAc, washed with H2O, sat. NaHCO3, brine, and dried (Na2SO4). Filtration through a 1″ pad of SiO2 and concentration provided 69 mg (100%) of 7.5. MS (ESI) 339.3 (MH+), 337.3 (MH−).

Workup

  1. customthe solution was quenched with MeOH
  2. additiondiluted with EtOAc
  3. washwashed with H2O, sat. NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration through a 1″
  6. concentrationpad of SiO2 and concentration

Sources & evidence

ORD record
ord-dea479939fe54724a3d5147aad328dc7
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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