Triphenylphosphine → HCID 86754649, compound

HRID 1740479Notes

Reaction equation

HRID 1740479 reaction equation
[C:1]([N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=O)[NH:12][C:10]1=[O:11])(=[O:8])[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:37]([O:41][C:42]([N:44]1[CH2:48][C@@H:47]([N:49]2[C:53](=[O:54])[C:52]3=[CH:55][CH:56]=[CH:57][CH:58]=[C:51]3[C:50]2=[O:59])[CH2:46][C@@H:45]1[CH2:60]O)=[O:43])([CH3:40])([CH3:39])[CH3:38].CC[O:64]C(/N=N/C(OCC)=O)=O.[Al]>C1COCC1>[C:37]([O:41][C:42]([N:44]1[CH2:48][C@@H:47]([N:49]2[C:50](=[O:59])[C:51]3=[CH:58][CH:57]=[CH:56][CH:55]=[C:52]3[C:53]2=[O:54])[CH2:46][C@@H:45]1[CH2:60][N:12]1[CH:13]=[C:15]([CH3:16])[C:17](=[O:64])[N:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]1=[O:11])=[O:43])([CH3:40])([CH3:38])[CH3:39]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 667610benzoylthymineHCID 5359268AluminumHCID 5462977Diethyl azodicarboxylateHCID 56635400HCID 56635400, compound

Product 1

HCID 86754649HCID 86754649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N3 -benzoylthymine 20 (1.15 g, 5 mmol) in dry THF (70 ml) under argon was added triphenyl phosphine (2.62 g, 10 mmol) and (2R,4S)-1-(tert-Butyloxycarbonyl)-2-hydroxymethyl-4-phthalimido-pyrrolidine (1.4 g, 4.05 mmol) at room temperature. After 15 min, diethylazodicarboxylate (1.74 g, 10 mmol) was added slowly during 10 min period. The reaction mixture was covered with aluminum foil and allowed to stir at room temperature under argon for 24 h. The solvent was evaporated to dryness and the residue dissolved in EtOAc (150 ml). The organic extract was washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine (100 ml), and dried over anhydrous Na2SO4. The dried EtOAc extract was evaporated to dryness to give an orange oil. The crude product was purified by flash chromatography over silica gel using hexane→EtOAc as the eluent. The fraction having the required product was pooled and evaporated to give a pale pink oil. Yield: 2.0 g (89%). 1HNMR (CDCl3): 1.41 (s, 9H, Boc), 1.72 (s, 3H, CH3), 1.90 (dd, 1H), 2.34 (m, 1H), 3.40-3.62 (m, 3H), 4.00 (m, 2H), 4.28 (bs, 1H), 4.44 (m, 1H), 7.06 (s, 1H, C6H) and 7.20-7.60 (m, 9H, Ph).

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue dissolved in EtOAc (150 ml)
  3. extractionThe organic extract
  4. washwas washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine (100 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. extractionThe dried EtOAc extract
  7. customwas evaporated to dryness
  8. customto give an orange oil
  9. customThe crude product was purified by flash chromatography over silica gel
  10. customevaporated
  11. customto give a pale pink oil

Sources & evidence

ORD record
ord-b14486a253ef4ee694afb2cb5a15a677
Source dataset
uspto-grants-1999_10
Patent number
US05969135

Reaction notes

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