HCID 136404621, compound → HCID 136404620, compound

HRID 1604244Notes

Reaction equation

HRID 1604244 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:37])[C:5]2[S:10][C:9](=[S: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](=[S: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 136404621HCID 136404621, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 136404620HCID 136404620, 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)-thione (0.18 g, 0.33 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 aqueous EtOH; 0.068 g (0.178 mmol, 54%), mp 240-242° C. (dec). Ir (KBr): ν3210-3410 (OH, NH2), 1685 (C=O), and 1630 (C=S) cm-1 ; Uv, λmax (nm) (ε×10-3): pH 1, 352 (6.5), 291 (3.2), 264 (5.1), 244 (5.4), 216 (5.5); pH 7, 356 (6.2), 264 (5.1), 244 (5.5); pH 11, 356 (6.1), 264 (5.1), 244 (5.6). 1H nmr (DMSO-d6): δ3.74 (m, 3H, C5'H2 and C4'H), 4.72 (t, 1H, C5'OH), 4.90 (m, 1H, C3'H), 5.25 (q, 1H, C2'H), 5.58 (d, 1H, C3'OH), 6.93 (s, 2H, NH2), 7.10 (t, J1',2' =7.6 Hz, 1H, C1'H), 11.53 (s, 1H, NH). Anal. Calc'd for C10H11FN4O4S2.C2H5OH (380.41): C, 37.88; H, 4.50; N, 14.73; S, 16.85; F, 4.99. Found: C, 37.72; H, 4.17; N, 14.93; S, 16.54; F, 5.16.

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 aqueous EtOH

Sources & evidence

ORD record
ord-3421f550d5714404923b8b7bf46d527b
Source dataset
uspto-grants-1999_11
Patent number
US05994321

Reaction notes

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