Triphenylphosphine → HCID 54131397, compound

HRID 399956Notes

Reaction equation

HRID 399956 reaction equation
[C:1]([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:21](O)[CH2:20]1)(=[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.[Li][N:55]=[N+:56]=[N-:57].CCOC(/N=N/C(OCC)=O)=O>CN(C=O)C>[C:27]([O:26][CH2:25][C@H:23]1[O:24][C@@H:19]([N:14]2[C:15]3[N:16]=[CH:17][N:18]=[C:10]([NH:9][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:11]=3[N:12]=[CH:13]2)[CH2:20][C@@H:21]1[N:55]=[N+:56]=[N-:57])(=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 13964206HCID 13964206, compoundHCID 178506933HCID 178506933, compound

Product 1

HCID 54131397HCID 54131397, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N6 -Benzoyl-9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine (7.0 g, 15.3 mmol), triphenylphosphine (6.0 g, 22.9 mmol), and LiN3 (2.8 g, 56.4 mmol) were dissolved in DMF (100 mL). To this stirring mixture was added diethylazodicarboxylate (3.6 mL, 22.9 mmol) in one portion, the reaction was stirred for 2.5 h at RT, and the reaction was quenched with H2O (10 mL). The solvents were removed in vacuo, the residual oil was redissolved in EtOAc (300 mL) and extracted with H2O (2×200 mL) and saturated. aq. NaCl (200 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residual oil was purified on SiO2 (2-5% MeOH/CH2 Cl2) to afford 5'-O-Benzoyl-N6 -benzoyl-3'-azido-2',3'-dideoxyadenosine, 1a, as an amber foam, which was taken on directly to hydrogenation.

Workup

  1. customthe reaction was quenched with H2O (10 mL)
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residual oil was redissolved in EtOAc (300 mL)
  4. extractionextracted with H2O (2×200 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residual oil was purified on SiO2 (2-5% MeOH/CH2 Cl2)

Sources & evidence

ORD record
ord-1a4ef56b595a460b99f6971772090ab5
Source dataset
uspto-grants-1998_10
Patent number
US05824793

Reaction notes

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