Hydrochloric Acid → Batzelline A

HRID 1086181Notes

Reaction equation

HRID 1086181 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[C:5]2[CH2:9][CH2:10][N:11]=[C:12]3[C:13]([Cl:18])=[C:14](N)[C:15](=[O:16])[C:3]1=[C:4]23.N([O-])=[O:20].[Na+].Cl>CC(O)=O.O1CCOCC1.O>[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[C:5]2[CH2:9][CH2:10][NH:11][C:12]3=[C:13]([Cl:18])[C:14]([C:15](=[O:16])[C:3]1=[C:4]23)=[O:20]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10085148HCID 10085148, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 180158Batzelline AYield 19.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 20 mg of isobatzelline A in 2 ml of HOAc and 1 ml of dioxane is allowed to react with 20 mg of NaNO2 in 5 ml of H2O at 0° C. for 2 hours. After addition of 3 ml of 1N HCl, the solution was stirred at room temperature overnight, and extracted with 10 ml CHCl3 /MeOH (1:1) twice. The concentrated extract was further fractionated on a Superco LC-NH2 column (50 ml×3 ml) with 1% MeOH/CHCl3, and subsequently purified on a HPLC LiChrosorb-NH2 column (3% MeOH/CHCl3) to give 4 mg of batzelline A.

Workup

  1. extractionextracted with 10 ml CHCl3 /MeOH (1:1) twice
  2. extractionThe concentrated extract
  3. customsubsequently purified on a HPLC LiChrosorb-NH2 column (3% MeOH/CHCl3)

Sources & evidence

ORD record
ord-0cf8fa2ab9d94d7f9ea6f0dbc26b3a36
Source dataset
uspto-grants-1991_07
Patent number
US05028613

Reaction notes

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