Isoamyl Nitrite → HCID 59302559, compound

HRID 2237442Notes

Reaction equation

HRID 2237442 reaction equation
C(OC([C:6]1[S:20][C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=2[C:7]=1[OH:21])=O)C.N(O[CH2:25]CC(C)C)=O>C(O)(C(F)(F)F)=O.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][C:8]2[C:7]([O:21][CH3:25])=[CH:6][S:20][C:9]=2[CH2:10][CH2:11]1)=[O:16])[CH3:19]

Participants

5

Reactant 2

HCID 8053Isoamyl NitriteHCID 59302577HCID 59302577, compound

Product 1

HCID 59302559HCID 59302559, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

The product from step b) (256 mg, 0.69 mmol) was stirred in TFA (2 mL) for 30 minutes. The reaction was concentrated and dissolved in EtOH (5 mL). Isoamyl nitrite (140 μL, 1.04 mmol) and Cu(OAc)2 (188 mg, 1.04 mmol) were added to the solution and the reaction was stirred at room temperature overnight. The reaction was filtered through a silica plug and purified by silica gel chromatography (EtOAc/Hex-gradient) to give 17 mg of the subtitle compound. MS: ESI (positive): 271 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in EtOH (5 mL)
  3. filtrationThe reaction was filtered through a silica plug
  4. custompurified by silica gel chromatography (EtOAc/Hex-gradient)

Sources & evidence

ORD record
ord-6a4d255c09d743258f5dd146e45038c8
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

Loading…