HCID 18666645, compound → HCID 18661325, compound

HRID 355503Notes

Reaction equation

HRID 355503 reaction equation
[C:1]([O:9][C@@H:10]1[C@@H:14]([CH2:15][O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:13][CH:12]([N:25]=[N+]=[N-])[C@H:11]1[F:28])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>O1CCOCC1.[Pd]>[C:1]([O:9][C@@H:10]1[C@@H:14]([CH2:15][O:16][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:13][CH:12]([NH2:25])[C@H:11]1[F:28])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 18666645HCID 18666645, compound3×HCID 178418361HCID 178418361, compound

Product 1

HCID 18661325HCID 18661325, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

3.5-Di-O-benzoyl-2-deoxy-2-fluoro-α,β-D-arabinofuranosyl azide [compound (7)] (see Example 2 of PCT International Laid-Open publication WO 93/10137 specification of PCT/JP 92/01489 application) in the form of a colorless syrup (350 mg) was dissolved in dioxane (7 ml). Into this solution, hydrogen was blown at room temperature in the presence as catalyst of palladium black for 1 hour to conduct the catalytic reduction intended, thereby convert the azido group of compound (7) into amino group. The reaction solution obtained was filtered and the filtrate was concentrated up to about a half volume thereof, and then diluted with dichloroethane (50 ml). The diluted solution was dried over calcium chloride, and then a small amount of triethylamine was added thereto, followed by concentration to afford the titled compound (8) as a colorless syrup (324 mg). Crude yield: 99%.

Workup

  1. customThe reaction solution obtained
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated up to about a half volume
  4. additiondiluted with dichloroethane (50 ml)
  5. dry with materialThe diluted solution was dried over calcium chloride
  6. additiona small amount of triethylamine was added
  7. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-d320791e21b949c4b947ff1709992a04
Source dataset
uspto-grants-1998_11
Patent number
US05831072

Reaction notes

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