Triphenylphosphine → HCID 178471300, compound

HRID 1860669Notes

Reaction equation

HRID 1860669 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([CH3:34])([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:55][CH2:56][CH2:57][NH:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][N+:60]=1[O-:65]>C1COCC1>[CH3:34][C:21]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)([CH2:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][CH2:55][CH2:56][CH2:57][NH:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][N+:60]=2[O-:65])=[CH:19][CH:18]=1)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18624169HCID 18624169, compoundHCID 178526251HCID 178526251, compound

Product 1

HCID 178471300HCID 178471300, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (157 mg, 0.9 mmol) in 2 ml THF was added to a solution of the product of STEP 7 (197 mg, 0.66 mmol) and triphenylphosphine (236 mg, 0.9 mmol) in 5 ml THF at room temperature and stirred for 15 min. 2-(3-Hydroxypropylamino)pyridine N-oxide (168 mg, 0.9 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, CH2Cl2/CH3OH/NH4OH-98.5/1/0.5) to afford a clean product in 154 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 was purified by chromatography (on silica gel, CH2Cl2/CH3OH/NH4OH-98.5/1/0.5)
  4. customto afford a clean product in 154 mg

Sources & evidence

ORD record
ord-440aae1b4d8f4dd492fe228cfd14d8b3
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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