Triphenylphosphine → HCID 178471327, compound

HRID 1860677Notes

Reaction equation

HRID 1860677 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][C:15]=1[O:30][CH3:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:52][CH2:53][CH2:54][NH:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][N+:57]=1[O-:62]>C1COCC1>[CH3:31][O:30][C:15]1[CH:16]=[C:17]([CH2:20][C:21]([CH3:28])([CH3:29])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=[CH:19][C:14]=1[O:13][CH2:52][CH2:53][CH2:54][NH:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][N+:57]=1[O-:62]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18624199Ethyl 4-(4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutanoateHCID 178526251HCID 178526251, compound

Product 1

HCID 178471327HCID 178471327, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (174 mg, 1.0 mmol) in 3 ml THF was added to a solution of the product of STEP 6 (18 mg, 0.676 mmol) and triphenylphosphine (262 mg, 1.0 mmol) in 7 ml THF at room temperature and stirred for 15 min. 2-(3-Hydroxypropylamino)pyridine N-oxide (168 mg, 1.0 mmol) was added. The reaction was stirred at room temperature for 18 h. THF was evaporated and the residue purified by chromatography (on silica gel, C2HC2I/CH3OH/NH4OH=97.5/2/0.5) to afford a pale brown oil in 81.5 mg). 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 purified by chromatography (on silica gel, C2HC2I/CH3OH/NH4OH=97.5/2/0.5)
  4. customto afford a pale brown oil in 81.5 mg)

Sources & evidence

ORD record
ord-abe1a71fee4d46b6ace5f4ed88ec59f2
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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