Triphenylphosphine → HCID 59923480, compound

HRID 2297724Notes

Reaction equation

HRID 2297724 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([OH:35])(=[S:34])[CH3:33].C(=O)([O-])O.[Na+].O[CH2:42][CH2:43][N:44]([CH2:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:45](=[O:61])[NH:46][C@@H:47]([CH2:57][CH:58]([CH3:60])[CH3:59])[C:48]([N:50]1[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]1)=[O:49]>O1CCCC1>[C:32]([S:34][CH2:42][CH2:43][N:44]([CH2:62][CH2:63][C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)[C:45](=[O:61])[NH:46][C@@H:47]([CH2:57][CH:58]([CH3:59])[CH3:60])[C:48]([N:50]1[CH2:51][CH2:52][N:53]([CH3:56])[CH2:54][CH2:55]1)=[O:49])(=[O:35])[CH3:33]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 516892Sodium BicarbonateHCID 18337250HCID 18337250, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 59923480HCID 59923480, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In anhydrous tetrahydrofuran (3 ml) are dissolved 1-[(2S)-2-[3-(2-hydroxyethyl)-3-phenethylureido]-4-methylvaleryl]-4-methylpiperazine (Compound No. 18-1, 500 mg) and triphenylphosphine (654 mg) under a nitrogen atmosphere, and the solution is stirred under salt-ice cooling for 30 minutes. To the solution are added a solution of diethyl azodicarboxylate (435 mg) in anhydrous tetrahydrofuran (1 ml) and a solution of thioacetic acid (0.2 ml) in anhydrous tetrahydrofuran (2 ml) successively dropwise while keeping liquid temperature at 5° C. The mixture is stirred for one hour, a 10% aqueous sodium hydrogencarbonate solution is added to the reaction mixture, and the whole is extracted with ether. The organic layer is washed with a 10% aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 472 mg (82%) of the titled compound (Compound No. 27-1).

Workup

  1. customat 5° C
  2. extractionthe whole is extracted with ether
  3. washThe organic layer is washed with a 10% aqueous sodium hydrogencarbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b57aef9d90fb47ef98a07245d78332e8
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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