Hexachloroethane → HCID 86687034, compound

HRID 1402173Notes

Reaction equation

HRID 1402173 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10]([C@:12]2([CH3:18])[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])=O)=[N:6][CH:7]=1.CCN(CC)CC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[CH3:17][N:13]1[CH2:14][CH2:15][CH2:16][C@:12]1([C:10]1[N:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]2=[N:8][N:9]=1)[CH3:18]

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86687033HCID 86687033, compound

Product 1

HCID 86687034HCID 86687034, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Intermediate 47a (668 mg, 2.64 mmol), Et3N (1.5 mL, 11 mmol) and Ph3P (1.4 g, 5.3 mmol) in THF (20 mL) at 0° C. was added hexachloroethane (1.25 g, 5.29 mmol). The mixture was stirred at 0° C. for 10 min, then at RT for 1 h. The mixture was partitioned between EtOAc/water and the aqueous extracted with EtOAc. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Purification by FCC, using 0-10% MeOH in EtOAc, gave the title compound as a pale brown solid (300 mg, 49%). LCMS (Method 4): Rt 0.39, m/z 235 [MH+].

Workup

  1. waitat RT for 1 h
  2. customThe mixture was partitioned between EtOAc/water
  3. extractionthe aqueous extracted with EtOAc
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by FCC

Sources & evidence

ORD record
ord-141a59d7053741ddbc82fcbc0eece52c
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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