Pyridine → HCID 72247373, compound

HRID 2191004Notes

Reaction equation

HRID 2191004 reaction equation
O[CH2:2][CH:3]1[CH:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][CH:6]2[CH:5]([N:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:16]=3[N:15]=[N:14]2)[O:4]1.C1CCC(N=C=NC2CCCCC2)CC1.N1C=CC=CC=1.[CH2:52]([O:54][P:55]([CH:60]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:59])[O:56][CH2:57][CH3:58])[CH3:53]>CS(C)=O.C(Cl)Cl>[CH2:52]([O:54][P:55]([CH:60]=[CH:2][CH:3]1[CH:7]2[CH:6]([O:10][C:9]([CH3:11])([CH3:12])[O:8]2)[CH:5]([N:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:16]=3[N:15]=[N:14]2)[O:4]1)(=[O:59])[O:56][CH2:57][CH3:58])[CH3:53]

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 10573715Diethyl(triphenylphosphoranylidene)methylphosphonateHCID 68592696HCID 68592696, compound

Product 1

HCID 72247373HCID 72247373, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 6.3 (1.2 g, 2.91 mmol) was dissolved in 23 mL DMSO, and treated with DCC (3.6 g, 17.5 mmol) and DCA (0.24 mL, 2.91 mmol). The mixture was stirred for 2 h and then treated with 0.3 mL pyridine. Diethyl(triphenylphosphoranylidene)methylphosphonate (2.9 g, 6.98 mmol) was dissolved in 5 mL CH2Cl2 and it was added to the mixture dropwise and the mixture was stirred for 3 h. The mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed with H2O three times, dried over MgSO4, filtered and concentrated down under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 100% EtOAc to 5% MeOH in EtOAc to give compound 6.4 (469 mg, 30% yield). 1HNMR (300 MHz, CD3OD) δ 1.17-1.35 (m, 6H), 1.46 (s, 3H), 1.64 (s, 3H), 3.85-3.97 (m, 4H), 4.04-4.12 (m, 1H), 5.01 (m, 1H), 5.33-5.45 (m, 2H), 5.81 (d, 1H, J=5.7), 6.63-6.77 (m. 1H), 7.57-8.12 (m, 5H), 8.87 (s, 1H). LRMS (ESI) MH+ C24H29N6O7P requires 545.2, Found 545.0.

Workup

  1. additionit was added to the mixture dropwise
  2. stirringthe mixture was stirred for 3 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organic layer was washed with H2O three times
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated down under reduced pressure
  9. washeluting with 100% EtOAc to 5% MeOH in EtOAc

Sources & evidence

ORD record
ord-2ae181d1a97e4f36a2596ade115ced2e
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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