Sodium ethoxide → HCID 178467392, compound

HRID 892115Notes

Reaction equation

HRID 892115 reaction equation
[C:1]([C:5]1[NH:13][C:12]2[C:7](=[N:8][C:9](S(C)(=O)=O)=[N:10][C:11]=2[NH:14][C@H:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:16]O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[O-:29][CH2:30][CH3:31].[Na+]>C(O)C>[CH2:18]([C@@H:15]1[CH2:16][N:10]2[C:11]([C:12]3[NH:13][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6][C:7]=3[N:8]=[C:9]2[O:29][CH2:30][CH3:31])=[N:14]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 69662579HCID 69662579, compound

Product 1

HCID 178467392HCID 178467392, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

In a manner similar to that in Example 66, a cyclized compound was obtained from Compound C8 prepared in Reference Example 43, to a solution of the cyclized compound (4.88 g, 14.3 mmol) in ethanol (30 mL) was added a 21% solution of sodium ethoxide (30 mL, 93.0 mmol, 6.5 equivalents) in ethanol, and then the mixture was stirred with heating at 70° C. for 3 hours. The reaction solution was concentrated, and the deposited crystals were collected by filtration and recrystallized from ethyl acetate to obtain the title compound (2.67 g, 54%) as white crystals.

Workup

  1. concentrationThe reaction solution was concentrated
  2. filtrationthe deposited crystals were collected by filtration
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c51871637c2d49e08019794ccdb68872
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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