Acetic Acid → HCID 60030251, compound

HRID 1825286Notes

Reaction equation

HRID 1825286 reaction equation
CC1C=CC(C([O:8][CH2:9][C@@H:10]2[CH:14]([O:15]C(C3C=CC(C)=CC=3)=O)[CH2:13][C@H:12]([N:25]3[C:29]4=[N:30][C:31]([NH2:36])=[N:32][C:33]([O:34][CH3:35])=[C:28]4[C:27]([I:37])=[N:26]3)[O:11]2)=O)=CC=1.C[O-].[Na+].C(O)(=O)C>CO>[NH2:36][C:31]1[N:30]=[C:29]2[N:25]([C@@H:12]3[O:11][C@H:10]([CH2:9][OH:8])[CH:14]([OH:15])[CH2:13]3)[N:26]=[C:27]([I:37])[C:28]2=[C:33]([O:34][CH3:35])[N:32]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 86597505HCID 86597505, compound

Product 1

HCID 60030251HCID 60030251, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a suspension of 15 (32.4 g, 50.40 mmol) in 600 mL of methanol was added 12.5 mL of 1M sodium methoxide in methanol. The reaction mixture was stirred at reflux for 18 h. and then cooled in a freezer (−10° C.). The crystals of 3 that formed were filtered and rinsed with ice-cold methanol: 10.95 g yield. Acetic acid (12.5 mL) was added to the filtrate and the volume was reduced to about 300 mL. The solution was allowed to sit in the freezer overnight and another crop of crystals (3.95 g) was collected. The filtrate was evaporated to dryness and the residual oil was triturated in ether. The solid that formed was filtered, dried and recrystallized from boiling water: 2.03 g. Total yield=16.93 g (83%); TLC (10% methanol in ethyl acetate), Rf=0.23; 1H NMR (DMSO-d6) δ 7.02 (2H, br s, 6-amino), 6.33 (1H, t, J=6.1 Hz), 5.24 (1H, d, J=4.4 Hz, 3′-OH), 4.73 (1H, t, J=5.6 Hz, 5′-OH), 4.36 (1H, m, 3′-H), 3.99 (3H, s, 4-methoxy), 3.75 (1H, m, 4′-H), 3.51–3.32 (2H, m, 5′-Hs), 2.79 and 2.17 (2H, 2×m, 2′-Hs). Anal. Calcd. For C11H141N5O4 0.3H2O; C, 32.02; H, 3.57; N, 16.98. Found C, 32.13; H, 3.35; N, 16.77.

Workup

  1. temperatureat reflux for 18 h.
  2. customThe crystals of 3 that formed
  3. filtrationwere filtered
  4. washrinsed with ice-cold methanol
  5. custom10.95 g yield
  6. customto sit in the freezer overnight
  7. customanother crop of crystals (3.95 g) was collected
  8. customThe filtrate was evaporated to dryness
  9. customthe residual oil was triturated in ether
  10. customThe solid that formed
  11. filtrationwas filtered
  12. customdried
  13. customrecrystallized

Sources & evidence

ORD record
ord-1df4a729fa434a199aff2f5231d3b2b6
Source dataset
uspto-grants-2006_05
Patent number
US07045610B2

Reaction notes

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