Triphenylphosphine → HCID 10405219, compound

HRID 1295693Notes

Reaction equation

HRID 1295693 reaction equation
CN(C(/N=N/C(N(C)C)=O)=O)C.C(OC([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:27]([O:32]CCO)=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21]1)=O)(C)(C)C.[C:36]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:37]=1.[CH2:55]1[O:59][C:58]2[CH:60]=[C:61]([OH:64])[CH:62]=[CH:63][C:57]=2[O:56]1>C1COCC1>[O:56]1[C:57]2[CH:63]=[CH:62][C:61]([O:64][CH2:36][CH2:37][N:28]3[CH:29]=[CH:30][N:31]=[C:26]([N:23]4[CH2:22][CH2:21][NH:20][CH2:25][CH2:24]4)[C:27]3=[O:32])=[CH:60][C:58]=2[O:59][CH2:55]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 68289SesamolHCID 5353800DiamideHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 10405219HCID 10405219, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TMAD (0.207 g, 1.20 mmol) was added to a solution of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-pyrazinyloxy]ethanol (0.324 g, 1.00 mmol), triphenylphosphine (0.315 g, 1.20 mmol) and sesamol (0.173 g, 1.25 mmol) in THF (1 mL) at room temperature. After being stirred for 2 h, the reaction mixture was concentrated and put through a silica column using toluene/EtOAc (7:3) as eluent. Solvents were removed in vacuo and the resulting N-t-BOC derivative was treated with dichloromethane/TFA/H2O (50:45:5; 5 mL) for 15 min with stirring. The mixture was concentrated and the residue purified by chromatography on silica gel using EtOAc/HOAc/MeOH/H2O (20:3:3:2) as eluent. The product-containing fractions were concentrated, washed between dichloromethane/5% aqueous NaOH, and put through a silica column using dichloromethane/MeOH (8:2) to give 78 mg (23%) of the title compound. HRMS m/z calcd for C17H20N4O4 (M)+ 344.1485, found 344.1474.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customSolvents were removed in vacuo
  3. additionthe resulting N-t-BOC derivative was treated with dichloromethane/TFA/H2O (50:45:5; 5 mL) for 15 min
  4. stirringwith stirring
  5. concentrationThe mixture was concentrated
  6. customthe residue purified by chromatography on silica gel
  7. concentrationThe product-containing fractions were concentrated
  8. washwashed between dichloromethane/5% aqueous NaOH

Sources & evidence

ORD record
ord-ae0b5214c02f4c4e80c0a16c50a95ab7
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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