HCID 136404623, compound → HCID 136404622, compound

HRID 1604245Notes

Reaction equation

HRID 1604245 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:37])[C:5]2[S:10][C:9](=[Se:11])[N:8]([C@@H:12]3[O:25][C@H:24]([CH2:26][O:27]C(=O)C4C=CC=CC=4)[C@@H:14]([O:15]C(=O)C4C=CC=CC=4)[C@@H:13]3[F:36])[C:6]=2[N:7]=1.O(C)[Na]>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:37])[C:5]2[S:10][C:9](=[Se:11])[N:8]([C@@H:12]3[O:25][C@H:24]([CH2:26][OH:27])[C@@H:14]([OH:15])[C@@H:13]3[F:36])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 136404623HCID 136404623, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 136404622HCID 136404622, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-Amino-3-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-7-oxothiazolo[4,5-d]pyrimidine-2(3H,6H)-selone (0.3 g, 0.5 mmol), NaOCH3 (0.055 g) and anhydrous MeOH (60 mL) was stirred at room temperature for 16 h with the exclusion of moisture. The reaction mixture was neutralized with Amberlite IR-120(H+) ion-exchange resin. The resin was removed by filtration and the filtrate was evaporated to dryness. The residue was dissolved in MeOH (5 mL), adsorbed onto silica gel (5 g) and loaded on top of a prepacked (in CH2Cl2) silica gel column (2.8×15 cm). The column was flash eluted with CH2Cl2 :MeOH (9:1), the homogeneous product was isolated and crystallized from an acetone:toluene mixture; 0.15 g (0.383 mmol, 76%), mp 178-180° C. Ir (KBr): ν3200-3370 (OH, NH2), and 1630 (C=Se) cm-1. Uv, λmax (nm) (ε×10-3): pH 1, 376 (5.6), 286 (3.0), 220 (3.7); pH 7, 374 (5.5), 280 (3.9), 218 (3.8); pH 11, 374 (5.4), 280 (4.8), 234 (4.3). 1H nmr (DMSO-d6): δ3.76 (m, 3H, C5'H2 and C4'H), 4.72 (s, 1H, C5'OH), 4.91 (m, 1H, C3'H), 5.28 and 5.42 (tt, JH,F =55.6 Hz, JH,H =6.0 Hz, 1H, C2'H), 5.59 (d, 1H, C3'OH), 6.98 (s, 2H, NH2), 7.20 (t, J1',2' =7.6 Hz, 1H, C1'H), and 11.58 (s, 1H, NH). Anal. Calc'd for C10H11FN4O4SSE.0.11 toluene (391.41): C, 33.07; H, 3.06; N, 14.31. Found: C, 32.79; H, 3.06; N, 13.98.

Workup

  1. customThe resin was removed by filtration
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in MeOH (5 mL)
  4. washeluted with CH2Cl2 :MeOH (9:1)
  5. customthe homogeneous product was isolated
  6. customcrystallized from an acetone

Sources & evidence

ORD record
ord-b50eef9ed9c54017a65adc879f893c4a
Source dataset
uspto-grants-1999_11
Patent number
US05994321

Reaction notes

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