Hexane → HCID 135449112, compound

HRID 1886065Notes

Reaction equation

HRID 1886065 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-003d7346eb084830b550e177212acddc
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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