Triphenylphosphine → HCID 86705166, compound

HRID 2401260Notes

Reaction equation

HRID 2401260 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[CH2:33][C@@H:34]([NH:38][C:39]([NH:41][C:42]1[CH:43]=[N:44][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:46][CH:47]=1)=[O:40])[CH:35]([CH3:37])[CH3:36]>C1COCC1>[CH3:36][CH:35]([C@H:34]1[CH2:33][N:41]([C:42]2[CH:43]=[N:44][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:46][CH:47]=2)[C:39](=[O:40])[NH:38]1)[CH3:37]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86705165HCID 86705165, compound

Product 1

HCID 86705166HCID 86705166, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (770 mg) and diethyl azodicarboxylate (2.2 M solution in toluene, 1.3 mL) were added to a solution of 1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-3-[6-(trifluoromethyl)pyridin-3-yl]urea (640 mg) in THF (10 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, the residue was purified by column chromatography (silica gel cartridge and NH silica gel cartridge, hexane/ethyl acetate), and the resulting solid was washed with isopropyl ether to afford the title compound (500 mg). This product contained by-products originating in reaction reagents.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel cartridge and NH silica gel cartridge, hexane/ethyl acetate)
  3. washthe resulting solid was washed with isopropyl ether

Sources & evidence

ORD record
ord-faaebe45a57142d3973c21322a5094c9
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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