1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Bis(eta-cyclopentadienyl) iron

HRID 1454215Notes

Reaction equation

HRID 1454215 reaction equation
[C-:1]1([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.[Fe+2:21].CCN=C=NCCCN(C)C.Cl>CN(C=O)C.P([O-])([O-])([O-])=O>[C-:1]1([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5]1.[CH-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.[Fe+2:21].[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Fe+2:21]

Participants

6

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178525439HCID 178525439, compound

Product 2

HCID 7611Bis(eta-cyclopentadienyl) ironHCID 178525439HCID 178525439, compound

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

15 mg of the N-(ferrocenyl methyl)-6-amino caproic acid (Fc-aca) prepared in (1) of Example 8, 6 mg of N-hydrosuccinimide (NHS, Fluka Corp), and 9 mg of N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (EDC, Fluka Corp.) were dissolved in 0.3 mL of an anhydrous DMF solution and stirred for 30 minutes after the temperature was raised to 90° C. in a nitrogen atmosphere. The reaction was further performed for 30 minutes while the temperature of the solution was maintained at 80° C. 30 μL of the reaction mixture was added into a solution of 7 mg of lipase in 1 mL of a phosphate buffer solution (100 mM) at 2-minute intervals. The mixture was shaken at room temperature for a day and centrifuged to separate a precipitate. The filtrate was dialyzed in a 50-mM phosphate buffer solution (pH 7.4) for 30 hours to obtain an N-(ferrocenyl methyl)-6-amino caproic acid (Fc-aca)-bound lipase (ferrocene-bound lipase).

Workup

  1. waitThe reaction was further performed for 30 minutes while the temperature of the solution
  2. temperaturewas maintained at 80° C
  3. stirringThe mixture was shaken at room temperature for a day
  4. customto separate a precipitate
  5. customThe filtrate was dialyzed in a 50-mM phosphate buffer solution (pH 7.4) for 30 hours

Sources & evidence

ORD record
ord-6b5d4d5ae92e4ee09d03938c2d2ba29e
Source dataset
uspto-grants-2009_01
Patent number
US07479254B2

Reaction notes

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