Potassium Hydroxide → HCID 46199202, compound

HRID 2046028Notes

Reaction equation

HRID 2046028 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24]([CH2:26][N:27]5[CH2:30][CH:29]([C:31]([O:33]C)=[O:32])[CH2:28]5)=[CH:23][C:22]=4[CH:35]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[OH-].[K+]>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24]([CH2:26][N:27]5[CH2:28][CH:29]([C:31]([OH:33])=[O:32])[CH2:30]5)=[CH:23][C:22]=4[CH:35]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66614898HCID 66614898, compound

Product 1

HCID 46199202HCID 46199202, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product of Step A (0.06 g; 0.126 mmol) and 10% KOH (0.1 ml) in dioxane (2 ml) was refluxed for 1 h and solvents were evaporated to dryness. The residue was treated with AcOH (0.5 ml) and evaporated to dryness in vacuo. The residue was purified by FCC (SiO2, CH2Cl2 saturated with concentrated NH4OH and MeOH, 85:15) to give the title compound (0.032 g; 55%), as a colourless solid. 1H-NMR (CD3OD+CDCl3) 8.37 (d, 1H, J=3 Hz); 8.09 (dd, 1H, J=3, 6 Hz); 7.77 (dd, 1H, J=3, 9 Hz); 7.68 (s, 1H); 7.6 (d, 1H, J=9 Hz); 7.02-7.07 (m, 2H); 4.38 (s, 2H); 4.05-4.21 (m, 8H); 1.44-1.49 9m, 6H).

Workup

  1. temperaturewas refluxed for 1 h
  2. customsolvents were evaporated to dryness
  3. additionThe residue was treated with AcOH (0.5 ml)
  4. customevaporated to dryness in vacuo
  5. customThe residue was purified by FCC (SiO2, CH2Cl2 saturated with concentrated NH4OH and MeOH, 85:15)

Sources & evidence

ORD record
ord-b95e29cb8c0b419aafca552b6b82a1f4
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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