Hexachloroethane → HCID 86687197, compound

HRID 630913Notes

Reaction equation

HRID 630913 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[F:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][NH:17][C:18]([C@@H:20]2[CH2:25][CH2:24][CH2:23][CH2:22][N:21]2[CH3:26])=O)=[N:14][CH:15]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CO>[F:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:18]([C@@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][N:21]3[CH3:26])=[N:17][N:16]=2)[CH:15]=1

Participants

7

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86687196HCID 86687196, compound

Product 1

HCID 86687197HCID 86687197, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hexachloroethane (505 mg, 2.14 mmol) was added portionwise over 5 min at RT to a stirred mixture of Intermediate 120a (270 mg, 1.07 mmol), triethylamine (595 μL, 4.28 mmol) and triphenylphosphine (560 mg, 2.14 mmol) in THF (10 mL). The reaction mixture was stirred for 1.5 h and then diluted with methanol and loaded onto an SCX cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3 in MeOH and concentrated in vacuo. The resultant residue was purified by FCC on silica, using a gradient of 0-8% [2M NH3 in MeOH] in EtOAc to give the title compound (105 mg, 42%). 1H NMR (400 MHz, CDCl3): 1.34-1.51 (1H, m), 1.62-1.92 (5H, m), 2.00 (3H, s), 2.20 (1H, td, J=11.4, 3.7 Hz), 3.06 (1H, m), 3.87 (1H, dd, J=10.9, 3.3 Hz), 7.18 (1H, ddd, J=9.8, 7.6, 2.3 Hz), 7.71 (1H, ddd, J=9.9, 5.0, 0.7 Hz), 8.75-7.79 (1H, m).

Workup

  1. washThe cartridge was washed with MeOH
  2. washthe product eluted with 2M NH3 in MeOH
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by FCC on silica

Sources & evidence

ORD record
ord-1d9f2fdc4da84743ad459232b78800f6
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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