Triphenylphosphine → (S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurine

HRID 6269Notes

Reaction equation

HRID 6269 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:21][OH:22])[O:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]([O:46][C:47]([N:49]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C:50]1[N:58]=[C:57]2[C:53]([N:54]=[CH:55][N:56]2O)=[C:52]([O:60][CH3:61])[N:51]=1)=[O:48])([CH3:45])([CH3:44])[CH3:43].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:65]([O:64][C:62]([N:49]([C:47]([O:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:48])[C:50]1[N:58]=[C:57]2[C:53]([N:54]=[CH:55][N:56]2[O:22][CH2:21][C@@H:10]([O:11][CH2:12][P:13]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:20])[CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:52]([O:60][CH3:61])[N:51]=1)=[O:63])([CH3:68])([CH3:67])[CH3:66]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 145239662-[Bis-(t-butoxycarbonyl)amino]-9-hydroxy-6-methoxypurineHCID 53890153diethyl (R)-[2-benzyloxy-1-(hydroxymethyl)ethoxy]methylphosphonate

Product 1

HCID 53696618(S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurineYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of diethyl (R)-[2-benzyloxy-1-(hydroxymethyl)ethoxy]methylphosphonate (1.0 g, 3 mmol), triphenylphosphine (1.18 g, 4.5 mmol) and 2-[bis-(t-butoxycarbonyl)amino]-9-hydroxy-6-methoxypurine (1.15 g, 3 mmol) in dry THF (20 ml), cooled in ice and under a mitrogen atmosphere, was added, dropwise, diethyl azodicarboxylate (0.71 ml, 4.5 mmol). The resulting solution was allowed to warm to ambient temperature and left stirring for 16 hours. The solvent was evaporated under reduced pressure and the residue obtained chromatographed on silica gel using hexane/ethyl acetate 2:1 as eluant. The eluant was changed as follows: hexane/ethyl acetate 1:1, hexane/ethyl acetate 1:2 and finally to ethyl acetate to give (S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurine as a colourless oil (1.85 g, 88%).

Workup

  1. additionwas added
  2. waitleft
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue obtained
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-5bc3817b8fb84fdcb2e908b50be90647
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Reaction notes

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