Triphenylphosphine → HCID 19808649, compound

HRID 373897Notes

Reaction equation

HRID 373897 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18]([N:20]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:21]1[N:29]=[C:28]2[C:24]([N:25]=[CH:26][N:27]2[OH:30])=[C:23]([O:31][CH3:32])[N:22]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Si:59]([O:66][CH2:67][CH:68](O)[CH2:69][CH2:70][P:71](=[O:78])([O:75][CH2:76][CH3:77])[O:72][CH2:73][CH3:74])([C:62]([CH3:65])([CH3:64])[CH3:63])([CH3:61])[CH3:60]>O1CCCC1>[C:36]([O:35][C:33]([N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[C:21]1[N:29]=[C:28]2[C:24]([N:25]=[CH:26][N:27]2[O:30][CH:68]([CH2:67][O:66][Si:59]([C:62]([CH3:64])([CH3:63])[CH3:65])([CH3:60])[CH3:61])[CH2:69][CH2:70][P:71]([O:72][CH2:73][CH3:74])([O:75][CH2:76][CH3:77])=[O:78])=[C:23]([O:31][CH3:32])[N:22]=1)=[O:34])([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 145239662-[Bis-(t-butoxycarbonyl)amino]-9-hydroxy-6-methoxypurineHCID 19808612Diethyl 4-(t-butyldimethylsilyloxy)-3-hydroxybutylphosphonate

Product 1

HCID 19808649HCID 19808649, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.43 ml, 2.75 mmol) was added to a cooled mixture of 2-[bis-(t-butoxycarbonyl)-amino]-9-hydroxy-6-methoxypurine (0.71 g, 1.83 mmol), triphenylphosphine (0.72 g, 2.75 mmol) and diethyl 4-(t-butyldimethylsilyloxy)-3-hydroxybutylphosphonate (0.623 g, 1.83 mmol) in dry tetrahydrofuran (20 ml). The reaction mixture was stirred at ambient temperature for 1 hour, and then evaporated to dryness. The residue was dissolved in diethyl ether, the solution filtered, and the filtrate evaporated to give a yellow oil. This oil was partially purified by column chromatography on silica gel (eluting with dichloromethane:ethanol 97:3) to give 2-[bis-(t-butoxycarbonyl)amino]-9-[1-(t-butyldimethylsilyloxymethyl)-3-(diethoxyphosphoryl)propoxy]-6-methoxypurine as a yellow oil (1.20 g, 98%).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in diethyl ether
  3. filtrationthe solution filtered
  4. customthe filtrate evaporated
  5. customto give a yellow oil
  6. customThis oil was partially purified by column chromatography on silica gel (eluting with dichloromethane:ethanol 97:3)

Sources & evidence

ORD record
ord-ac1cbc0c0f91477dafa02139cf0e09f2
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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