6-Aminohexanoic Acid → Theophylline

HRID 1830490Notes

Reaction equation

HRID 1830490 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[NH:10][C:9](CCCC(O)=O)=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].CCN=C=NCCCN(C)C.Cl.C(CCN)CCC(O)=O.C(O)C(N)(CO)CO>C1N(CCS(O)(=O)=O)CCOC1>[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 5646-Aminohexanoic AcidHCID 6503Tris(hydroxymethyl)aminomethaneHCID 950361H-Purine-8-butanoic acid, 2,3,6,7-tetrahydro-1,3-dimethyl-2,6-dioxo- (9CI)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2153Theophylline

Reagents, catalysts & solvents 1

HCID 781654-Morpholineethanesulfonic acidSolvent2×

Procedure

1 mg of theophylline-8-butanoic acid (Sigma) was dissolved in 2 ml of a 0.1 M MES buffer solution. Thereafter, 3.6 mg of WSC hydrochloride and 2.5 mg of NHS were added thereto, and the mixture was stirred at room temperature for 15 minutes. Thereafter, 2.0 mg of ε Amino Caproic Acid (Sigma) was dissolved in 200 μl of 0.1 M MES, and the obtained solution was added to the above reaction product. The obtained mixture was reacted at room temperature for 2 hours. 100 μl of 1M Tris buffer solution (pH 7.5) was added to the mixture, and the reaction was terminated. Thereafter, the obtained reaction product was adsorbed to a column filled with 8 g of ODS silica (YMC-ODS-AQ 120A), followed by elution with a 30% methanol aqueous solution. The eluant was concentrated and then purified by medium-pressure separation chromatography (YAMAZEN Ultrapack ODS-S-4OB).

Workup

  1. additionthe obtained solution was added to the above reaction product
  2. customThe obtained mixture was reacted at room temperature for 2 hours
  3. customthe reaction was terminated
  4. customThereafter, the obtained reaction product
  5. additionfilled with 8 g of ODS silica (YMC-ODS-AQ 120A)
  6. washfollowed by elution with a 30% methanol aqueous solution
  7. concentrationThe eluant was concentrated
  8. custompurified by medium-pressure separation chromatography (YAMAZEN Ultrapack ODS-S-4OB)

Sources & evidence

ORD record
ord-2822074ea7a74295a5acbbe773edef3a
Source dataset
uspto-grants-2006_06
Patent number
US07067270B2

Reaction notes

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