Triphenylphosphine → HCID 86639844, compound

HRID 656257Notes

Reaction equation

HRID 656257 reaction equation
[N:1]([CH:4]([CH:27]1[O:31][C:30](=[O:32])[CH:29]([CH:33]([CH3:35])[CH3:34])[CH2:28]1)[CH2:5][CH:6]([CH:10]([C:12]1[CH:13]=[C:14]([Cl:26])[C:15]2[N:16]([C:18]([CH2:21][CH2:22][CH2:23][O:24][CH3:25])=[N:19][CH:20]=2)[CH:17]=1)[OH:11])[CH:7]([CH3:9])[CH3:8])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(C(C)C)C(C)C.[C:64](OC([O-])=O)([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65]>O1CCCC1.COC(C)(C)C.O>[Cl:26][C:14]1[C:15]2[N:16]([C:18]([CH2:21][CH2:22][CH2:23][O:24][CH3:25])=[N:19][CH:20]=2)[CH:17]=[C:12]([CH:10]([OH:11])[CH:6]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH:4]([NH:1][C:64](=[O:65])[O:66][C:67]([CH3:70])([CH3:69])[CH3:68])[CH:27]2[CH2:28][CH:29]([CH:33]([CH3:35])[CH3:34])[C:30](=[O:32])[O:31]2)[CH:13]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 22064466Tert-butyldicarbonateHCID 86639845HCID 86639845, compound

Product 1

HCID 86639844HCID 86639844, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

A solution of 2.72 mmol of 5-(1-azido-3-{[8-chloro-3-(3-methoxypropyl)imidazo[1,5-a]pyridin-6-yl]hydroxymethyl}-4-methylpentyl)-3-isopropyldihydrofuran-2-one in 15 ml of tetrahydrofuran is mixed with 3.264 mmol of triphenylphosphine and 0.064 ml of water. The reaction solution is stirred at room temperature for 16 hours. Water (0.40 ml) is added, and the reaction mixture is then heated to reflux for 8 hours. The reaction mixture is cooled to room temperature, diluted with tert-butyl methyl ether (100 Ml) and washed with brine (50 ml), dried with sodium sulphate and evaporated. The residue is dissolved in 20 ml of tetrahydrofuran, mixed with 4.08 mmol of Hünig's base and 3.264 mmol of tert-butyl dicarbonate and left to stand at room temperature for 12 hours. The reaction solution is diluted with tert-butyl methyl ether (50 ml) and washed with 0.1M HCl and brine, dried with sodium sulphate and evaporated. The title compound is identified by means of the Rf from the residue by flash chromatography (SiO2 60 F).

Workup

  1. temperaturethe reaction mixture is then heated
  2. temperatureto reflux for 8 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. washwashed with brine (50 ml)
  5. dry with materialdried with sodium sulphate
  6. customevaporated
  7. dissolutionThe residue is dissolved in 20 ml of tetrahydrofuran
  8. waitleft
  9. waitto stand at room temperature for 12 hours
  10. washwashed with 0.1M HCl and brine
  11. dry with materialdried with sodium sulphate
  12. customevaporated

Sources & evidence

ORD record
ord-6ab07ce771b945048c7d4944701e4cb9
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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