Hexachloroethane → HCID 89612150, compound

HRID 630777Notes

Reaction equation

HRID 630777 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:10]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH:17]([CH3:19])[CH3:18])=O)N)=[N:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC[N:41](CC)CC.ClC(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:8]([C:10]([C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[CH:17]([CH3:19])[CH3:18])=[N:41][N:6]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 117666055HCID 117666055, compound

Product 1

HCID 89612150HCID 89612150, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 58a (346 mg, 1.30 mmol), Ph3P (681 mg, 2.60 mmol) and Et3N (723 μL, 5.20 mmol) in THF (10.0 mL) at 0° C. was added hexachloroethane (616 mg, 2.60 mmol). The reaction was stirred at RT overnight then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was dissolved in MeOH and loaded onto an SCX-2 cartridge, which was washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo gave the title compound (220 mg, 68%). LCMS (Method 4): Rt 0.32 min, m/z 249.1 [MH+].

Workup

  1. customthen partitioned between EtOAc and water
  2. extractionThe aqueous layer was then extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in MeOH
  8. washwas washed with MeOH
  9. washThe product was eluted with 2M NH3 in MeOH
  10. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-a1fe95bc099e47b2a17a022128bd3be6
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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