Triphenylphosphine → HCID 86634377, compound

HRID 1191279Notes

Reaction equation

HRID 1191279 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([NH:27][CH:28]1[CH2:33][CH2:32][CH2:31][N:30]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH:29]1[CH2:44][CH2:45]O)=[O:26])([CH3:23])([CH3:22])[CH3:21].C1(P([N:61]=[N+:62]=[N-:63])(C2C=CC=CC=2)=O)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.O1CCCC1>[N:61]([CH2:45][CH2:44][CH:29]1[CH:28]([NH:27][C:25]([O:24][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:26])[CH2:33][CH2:32][CH2:31][N:30]1[C:34]([O:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:35])=[N+:62]=[N-:63]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86634376HCID 86634376, compound

Product 1

HCID 86634377HCID 86634377, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (202 mg) was added to the compound 14 (146 mg), tetrahydrofuran (1 mL), diphenylphosphoryl azide (0.17 mL) and 2.2 mol/L of a solution (0.35 mL) of diethyl azodicarboxylate in toluene with stirring at 0° C. The reaction solution was stirred at room temperature for 1 hour and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:3) to obtain the title compound (136 mg) having the following physical properties.

Workup

  1. stirringThe reaction solution was stirred at room temperature for 1 hour
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:3)

Sources & evidence

ORD record
ord-abebdbec76d74962a221b497154122fe
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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