Triphenylphosphine → HCID 58542327, compound

HRID 1951912Notes

Reaction equation

HRID 1951912 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:34]([O:41][C:42](=[O:63])[NH:43][C:44]1([CH2:47][N:48]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C@@H:49]([CH2:54]O)[CH2:50][CH:51]([CH3:53])[CH3:52])[CH2:46][CH2:45]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1(C)C=CC=CC=1>[CH2:50]([C@H:49]1[N:48]([C:56]([O:58][C:59]([CH3:60])([CH3:61])[CH3:62])=[O:57])[CH2:47][C:44]2([CH2:45][CH2:46]2)[N:43]([C:42]([O:41][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:63])[CH2:54]1)[CH:51]([CH3:52])[CH3:53]

Participants

5

Reactant 3

HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 58542369HCID 58542369, compound

Product 1

HCID 58542327HCID 58542327, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triphenylphosphine (1.57 g, 5.99 mmol) and diisopropyl azodicarboxylate (0.93 ml, 4.49 mmol) were added to a toluene (100 ml) solution of the compound (1.26 g, 3.00 mmol) obtained in Step 3 above under ice cooling and the resulting mixture was gradually returned to room temperature while being stirred for 18 hours. Further triphenylphosphine (1.57 g, 5.99 mmol) and diisopropyl azodicarboxylate (0.93 ml, 4.49 mmol) were added and the resulting mixture was heated to reflux for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=3:1 (v/v)] to give the title compound (0.57 g, 47%) as a colorless oil.

Workup

  1. customwas gradually returned to room temperature
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 4 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=3:1 (v/v)]

Sources & evidence

ORD record
ord-26bce44643844ab2a83dc76ed4503d93
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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