Ethanol → HCID 135542469, compound

HRID 1297510Notes

Reaction equation

HRID 1297510 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]#[N:15])[CH:10]([NH:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=1)[CH2:9][CH2:8]2)(=O)[CH3:2].C([OH:32])C.OO.[OH-].[Na+]>O>[CH3:2][C:1]1[NH:15][C:14](=[O:32])[C:13]2[C:5](=[CH:6][C:7]3[CH2:8][CH2:9][CH:10]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:28][CH:29]=4)[C:11]=3[CH:12]=2)[N:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 10971207HCID 10971207, compound

Product 1

HCID 135542469HCID 135542469, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 8 (1.33 g, 3.40 mmol), ethanol (15 ml), and water (3.1 ml) was cooled in an ice-bath, then 30% aqueous H2O2 solution (2.8 ml) was added followed by granulated sodium hydroxide pellets (0.230 g, 5.78 mmol). The reaction mixture was stirred at ˜0° C. for 10 min, then it was placed in an oil bath preheated to 55° C. and stirred at this temperature for 40 min. The reaction mixture was allowed to cool to room temperature, then the solvents were removed in vacuo and the residue was suspended in water (˜40 ml). The pH of this mixture was adjusted to ˜5 with 1N hydrochloric acid. The white precipitate was collected by filtration, washed with water, dried in vacuo over P2O5, then it was triturated with ether, collected by filtration and dried in vacuo. The title compound 9 was obtained as a white solid 1.11 g (83%), m.p. 277-281° C. (it melts with decomposition), (Found: C, 70.22; H, 6.43; N, 10.65; C23H25N3O3 requires C, 70.57; H, 6.44; N, 10.73%); δH ((CD3)2SO) 1.50 (9H, s, C(CH3)3), 2.31 (3H, s, Me), 1.87, 2.55 (each 1H, m, 7-H), 2.97 (2H, m, 8-H), 5.15 (1H, q, J 7.50, 6-H), 6.77 (2H, d, J 8.6, 3′,5′-H), 6.91 (1H, d, J 8.70, N10—H), 7.44, 7.87 (each 1H, s, 5-H, 9-H), 7.66 (2H, d, J 8.75, 2′,6′-H); m/z ESI) 783 {(2M+H)+, 100%}, 392 {(N+H)+, 30%}, 199 (90).

Workup

  1. temperaturewas cooled in an ice-bath
  2. customit was placed in an oil bath
  3. custompreheated to 55° C.
  4. stirringstirred at this temperature for 40 min
  5. temperatureto cool to room temperature
  6. customthe solvents were removed in vacuo
  7. filtrationThe white precipitate was collected by filtration
  8. washwashed with water
  9. dry with materialdried in vacuo over P2O5
  10. customit was triturated with ether
  11. filtrationcollected by filtration
  12. customdried in vacuo

Sources & evidence

ORD record
ord-4b9d30abd06c4cdc82d8cd7718f8b33c
Source dataset
uspto-grants-2007_07
Patent number
US07250511B2

Reaction notes

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