Sodium Hydroxide → HCID 178458771, compound

HRID 2089048Notes

Reaction equation

HRID 2089048 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([O:32][CH2:33][C:34]#[CH:35])[CH:30]=3)[N:25](S(C3C=CC=CC=3)(=O)=O)[CH:24]=2)[CH:3]=1.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([O:32][CH2:33][C:34]#[CH:35])[CH:30]=3)[NH:25][CH:24]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178458754HCID 178458754, compound

Product 1

HCID 178458771HCID 178458771, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 241a (0.056 g, 0.088 mmol) in dioxane (1.5 mL) was treated with 20% sodium hydroxide (0.10 mL, 0.088 mmol). The mixture was heated at 90 C for an hour. The solvent was evaporated. The residue was treated with 20% brine and twice extracted with dichloromethane. The layers were combined, dried with MgSO4 and concentrated to give 0.037 g of the title compound. The crude product was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated at 90 C for an hour
  2. customThe solvent was evaporated
  3. additionThe residue was treated with 20% brine
  4. extractiontwice extracted with dichloromethane
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-502bf67d3e924e9c82386908704d66ab
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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