Triphenylphosphine → HCID 18624186, compound

HRID 1860656Notes

Reaction equation

HRID 1860656 reaction equation
[N:1](C(OCC)=O)=NC(OCC)=O.[Br:13][C:14]1[CH:15]=[C:16]([CH2:22][C:23]([CH3:31])([CH3:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:17]=[C:18]([F:21])[C:19]=1[OH:20].[C:32]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:37]=CC=C[CH:33]=1.Cl.O1CCOCC1>C1COCC1.C(O)C>[NH2:1][CH2:33][CH2:32][CH2:37][O:20][C:19]1[C:18]([F:21])=[CH:17][C:16]([CH2:22][C:23]([CH3:30])([CH3:31])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:15][C:14]=1[Br:13]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18624189HCID 18624189, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 18624186HCID 18624186, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (0.488 g, 2.8 mmol) in 3 ml THF was added to a solution of the product of STEP 7 (0.72 g, 2.16 mmol) and triphenylphosphine (0.734 g, 2.8 mmol) in 13 ml THF at room temperature and stirred for 15 min. Tert-butyl N-(3-hydroxypropyl) carbamate (0.491 g, 2.8 mmol) was added. The reaction was stirred at room temperature for 18 h. THF was evaporated and the residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/4) to yield a golden oil in 0.87 g. This product was dissolved in 10 ml ethanol and 10 ml 4N HCl/dioxane and stirred at room temperature for 1 h. Solvents were evaporated to afford a light golden oil in 0.734 g. NMR spectra of the product were consistent for the proposed structure.

Workup

  1. stirringThe reaction was stirred at room temperature for 18 h
  2. customTHF was evaporated
  3. customthe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/4)
  4. customto yield a golden oil in 0.87 g
  5. customSolvents were evaporated
  6. customto afford a light golden oil in 0.734 g

Sources & evidence

ORD record
ord-86bfb0ce646d4619ae9aa00a5146875e
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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