Boron Trichloride → HCID 58655382, compound

HRID 2253252Notes

Reaction equation

HRID 2253252 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[S:35][C@H:34]([CH2:36][O:37]CC4C=CC(Cl)=CC=4Cl)[C@@H:23]([O:24]CC4C=CC(Cl)=CC=4Cl)[C@@H:12]3[O:13]CC3C=CC(Cl)=CC=3Cl)[C:4]=2[N:5]=[CH:6][N:7]=1.B(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[S:35][C@H:34]([CH2:36][OH:37])[C@@H:23]([OH:24])[C@@H:12]3[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 87735582HCID 87735582, compound

Product 1

HCID 58655382HCID 58655382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of compound 1-6 from Step F (1 eq) in dichloromethane at −78° C. is added boron trichloride (1M in dichloromethane, 10 eq) dropwise. The mixture is stirred at −78° C. then at −30° C. to −20° C. The reaction is quenched by addition of methanol/dichloromethane (1:1) and the resulting mixture stirred at −15° C., then neutralized with aqueous ammonia at 0° C. and stirred at room temperature. The solid is filtered and washed with CH2Cl2/MeOH (1/1). The combined filtrate and washings are evaporated, and the residue is purified by flash chromatography over silica gel using CH2Cl2 and CH2Cl2:MeOH gradient as the eluent to furnish the title compound 1-7.

Workup

  1. customat −30° C. to −20° C
  2. customThe reaction is quenched by addition of methanol/dichloromethane (1:1)
  3. stirringthe resulting mixture stirred at −15° C.
  4. customneutralized with aqueous ammonia at 0° C.
  5. stirringstirred at room temperature
  6. filtrationThe solid is filtered
  7. washwashed with CH2Cl2/MeOH (1/1)
  8. customThe combined filtrate and washings are evaporated
  9. customthe residue is purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-192a58170d0249bbac7ab53e52319fd9
Source dataset
uspto-grants-2008_01
Patent number
US07323449B2

Reaction notes

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