Hexane → HCID 135449112, compound

HRID 1440456Notes

Reaction equation

HRID 1440456 reaction equation
CC[O-].[Na+].[F:5][C:6]([F:23])([F:22])[C:7]([CH:9]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:10]([O:12]CC)=O)=O.Cl.[C:25]([NH2:28])(=[NH:27])[CH3:26].CCCCCC>CCO>[CH3:26][C:25]1[NH:28][C:10](=[O:12])[C:9]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:7]([C:6]([F:5])([F:22])[F:23])[N:27]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxideHCID 10636762Diethyl Trifluoroacetylglutarate

Product 1

HCID 135449112HCID 135449112, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of NaOEt (0.026 mol) in EtOH (prepared from 0.60 g of Na and 30 mL of EtOH) was added diethyl trifluoroacetylglutarate (3.70 g, 0.013 mol) and acetamidine hydrochloride (1.23 g, 0.013 mol). The reaction mixture was heated under reflux for 18 h , concentrated, and taken up in water. The mixture was acidified to pH 4 with 2N HCl and extracted with CH2Cl2. The extracts were dried (MgSO4) and concentrated to give a yellow solid. Trituration with hexane gave 0.87 g of product as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 h
  3. concentrationconcentrated
  4. extractionextracted with CH2Cl2
  5. dry with materialThe extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customto give a yellow solid

Sources & evidence

ORD record
ord-62eba33df0fb4c7a947df0c257f9f47a
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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