Potassium Hydroxide → 2,2'-(Hex-5-ynylazanediyl)diacetic acid

HRID 1622063Notes

Reaction equation

HRID 1622063 reaction equation
[CH2:1]([N:7]([CH2:13][C:14]([O:16]C)=[O:15])[CH2:8][C:9]([O:11]C)=[O:10])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[OH-].[K+]>C1COCC1>[CH2:1]([N:7]([CH2:13][C:14]([OH:16])=[O:15])[CH2:8][C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 87118843HCID 87118843, compound

Product 1

HCID 871187222,2'-(Hex-5-ynylazanediyl)diacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the obtained approximately 1.4 g dimethyl 2,2′-(hex-5-ynylazanediyl)diacetate was added 20 mL THF and 20 mL of 2 M KOH. The mixture was stirred overnight and monitored by TLC. The organic layer was separated, and the aqueous layer was quenched by addition of 20 mL of 2 M HCl. The solvent (H2O) was removed by rotary evaporation, and the resulting solid was dissolved into acetonitrile (ACN). The insoluble KCl salt was filtered, and the filtrate was concentrated by rotary evaporation. The final product of free acid was obtained as a greasy, transparent oil. Yield was quantitative. ESI-MS: [M+H]+ m/z 214.1.

Workup

  1. customThe organic layer was separated
  2. customthe aqueous layer was quenched by addition of 20 mL of 2 M HCl
  3. customThe solvent (H2O) was removed by rotary evaporation
  4. dissolutionthe resulting solid was dissolved into acetonitrile (ACN)
  5. filtrationThe insoluble KCl salt was filtered
  6. concentrationthe filtrate was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-349d142eb7e44a1580f1c236d3f0d03c
Source dataset
uspto-grants-2014_07
Patent number
US08778626B2

Reaction notes

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