تفاعل #836403

معادلة التفاعل

triethylamine

6-methoxy-α-methyl-2-naphthalenacetic acid

oxalylchloride

2-oxothiazolidin-4-carboxylic acid

→

expected product

المردود 68.5%

3-(6-methoxy-α-methyl-2-naphthalenacetyl)(R)-2-oxothiazolidin-4-carboxylic acid

المردود 68.5%

المذيبات

toluene

N,N-dimethylformamide

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter 2 hours at room temperature the solution is evaporated at reduced pressure
2. 2
   workup.DISSOLUTIONTo the solution of the obtained residue dissolved in tetrahydrofuran (50 ml) a mixture
3. 3
   workup.ADDITIONis added
4. 4
   غسيلThe reaction mixture is washed with HCl 5%
5. 5
   أخرىevaporated at reduced pressure
6. 6
   أخرىThe obtained residue is purified by chromatography on silica gel eluting with methylene chloride/methanol 95/5

الإجراء التجريبي

To a solution of 6-methoxy-α-methyl-2-naphthalenacetic acid (7.0 g, 30.4 mmoles) in toluene (100 ml) and N,N-dimethylformamide (10 ml) cooled at 0° C., oxalylchloride (5.23 ml, 61 mmoles) is added. After 2 hours at room temperature the solution is evaporated at reduced pressure. To the solution of the obtained residue dissolved in tetrahydrofuran (50 ml) a mixture is added consisting of 2-oxothiazolidin-4-carboxylic acid (4.07 g, 27.6 mmoles), 4-dimethylaminopyridine (0.84 g, 6.9 mmoles), triethylamine (7.69 ml, 55.2 mmoles) in tetrahydrofuran (50 ml) cooled at −10° C. The mixture is left at room temperature for 24 hours. The reaction mixture is washed with HCl 5%, then with water. The organic phase is anhydrified with sodium sulphate and then evaporated at reduced pressure. The obtained residue is purified by chromatography on silica gel eluting with methylene chloride/methanol 95/5. 6.79 g of the expected product are obtained in the form of an amorphous solid.

المصدر