Ammonia → HCID 54010489, compound

HRID 1267797Notes

Reaction equation

HRID 1267797 reaction equation
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[N:38]=[C:37]([C:39]([O:41]C)=O)[C:36]([C:43]([O:45]C)=O)=[N:35]1)(=O)C1C=CC=CC=1.[NH3:47].CO.[NH3:50]>>[C@H:11]1([N:34]2[N:35]=[C:36]([C:43]([NH2:47])=[O:45])[C:37]([C:39]([NH2:50])=[O:41])=[N:38]2)[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 12043120HCID 12043120, compoundHCID 21705897Ammonia methanol

Product 1

HCID 54010489HCID 54010489, compoundYield 89%

Conditions

Temperature
95 °C

Procedure

Compound 31 (6.0 g, 9.5 mmol) was dissolved in MeOH/NH3 (dry MeOH sat. with anhydrous NH3 at 0° C., 60 mL) were placed in a steel reaction vessel. The vessel was heated at 95° C. for 16 h. The reaction vessel was cooled, opened carefully and the NH3 was allowed to evaporate at room temperature. The MeOH was evaporated to dryness and the residue was triturated with hot toluene (3×50 mL) and filtered. The brown residue was crystallized from aqueous EtOH (95%) to furnish 2.40 g (89%) of 32: mp 210-212° C.; 1H NMR (Me2SO-d6) δ 3.45-3.59 (m, 2H, C5′H), 3.98 (m, 1H, C4.H), 4.25 (m, 1H, C3.H), 4.54 (m, 1H, C2′H), 4.78 (t, 1H, C5′OH, D2O exchangeable), 5.27 and 5.67 (2d, 2H, C2′,3′OH, D2O exchangeable), 5.89 (d, 1H, J1′,2′=3.85 Hz, C1′H), 8.05 and 9.05 (2br s, 4H, 2 CONH2). Anal. CaIc. for C9H13N5O6 (287.23): C, 37.63; H, 4.56; N, 24.38. Found: C, 37.52; H, 4.19; N. 24.59.

Workup

  1. temperatureThe reaction vessel was cooled
  2. customto evaporate at room temperature
  3. customThe MeOH was evaporated to dryness
  4. customthe residue was triturated with hot toluene (3×50 mL)
  5. filtrationfiltered
  6. customThe brown residue was crystallized from aqueous EtOH (95%)

Sources & evidence

ORD record
ord-b07803c69cfc474689f9ebc8fbf2d25b
Source dataset
uspto-grants-2003_04
Patent number
US06552183B1

Reaction notes

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