Hexachloroethane → HCID 86731377, compound

HRID 2277296Notes

Reaction equation

HRID 2277296 reaction equation
[Cl:1][C:2]1[CH:29]=[C:28]([O:30][CH2:31][CH:32]2[CH2:34][CH2:33]2)[CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:24]=C[C:10]([O:11][CH2:12][C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14])=[CH:9][C:8]=1O)=[O:5].ClC(Cl)(Cl)C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([N:64](CC)CC)C>C(#N)C.O>[Cl:1][C:2]1[CH:29]=[C:28]([O:30][CH2:31][CH:32]2[CH2:33][CH2:34]2)[CH:27]=[CH:26][C:3]=1[C:4]1[O:5][C:8]2[CH:9]=[C:10]([O:11][CH2:12][C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[CH3:14])[N:64]=[CH:24][C:7]=2[N:6]=1

Participants

7

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86731378HCID 86731378, compound

Product 1

HCID 86731377HCID 86731377, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl ((2S)-1-(4-((2-chloro-4-(cyclopropylmethoxy)benzoyl)amino)-3-hydroxyphenoxy)propan-2-yl)carbamate (200 mg), hexachloroethane (241 mg) and triphenylphosphine (321 mg) in acetonitrile (3 mL) was added triethylamine (0.454 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (65 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-eb86fd38f6cd442e8433328874f1a64a
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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