Chloroform → Coumarin 343 aminohexanoic Acid

HRID 2357108Notes

Reaction equation

HRID 2357108 reaction equation
[CH2:1]1[CH2:21][N:20]2[C:4]3[C:5]([CH2:17][CH2:18][CH2:19]2)=[C:6]2[O:13][C:11](=[O:12])[C:10]([C:14]([OH:16])=[O:15])=[CH:9][C:7]2=[CH:8][C:3]=3[CH2:2]1.C[O:23][C:24](=[O:31])[CH:25]([NH2:30])[CH2:26][CH2:27][CH2:28][CH3:29].ClC(Cl)Cl>P([O-])([O-])([O-])=O>[CH2:1]1[CH2:21][N:20]2[C:4]3[C:5]([CH2:17][CH2:18][CH2:19]2)=[C:6]2[O:13][C:11](=[O:12])[C:10]([C:14]([OH:16])=[O:15])=[CH:9][C:7]2=[CH:8][C:3]=3[CH2:2]1.[NH2:30][CH:25]([CH2:26][CH2:27][CH2:28][CH3:29])[C:24]([OH:31])=[O:23]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 131728252Coumarin 343 aminohexanoic acid-methyl ester

Product 1

HCID 131728251Coumarin 343 aminohexanoic Acid

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Coumarin 343-aminohexanoic acid-methyl ester (0.1 mmol) was dissolved in 200 ml phosphate buffer (10 mM, pH 7.0) and 20 mg esterase was added (EC 3.1.1.1.; Sigma No: E-3019). After stirring for three days at ambient conditions (room temperature) the methyl ester has been cleaved quantitatively. The product was isolated by extraction of the aqueous phase with trichloromethane. The separated organic phase was washed with H2O and brine (H2O saturated with NaCI). After drying over magnesium sulfate and removal of the solvent in a vacuum on a rotary evaporator, the residuum is dissolved in dioxane and lyophilized.

Workup

  1. addition20 mg esterase was added (EC 3.1.1.1.; Sigma No: E-3019)
  2. washThe separated organic phase was washed with H2O and brine (H2O saturated with NaCI)
  3. dry with materialAfter drying over magnesium sulfate and removal of the solvent in a vacuum on a rotary evaporator
  4. dissolutionthe residuum is dissolved in dioxane

Sources & evidence

ORD record
ord-acf620268bb54cea9cf71e8c5385d44a
Source dataset
uspto-grants-2010_07
Patent number
US07759470B2

Reaction notes

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