تفاعل #993082

معادلة التفاعل

EtOAc

4-hydroxy-7-(methoxycarbonyl)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

glycine benzyl ester hydrochloride

diisopropylethylamine

→

desired product

المردود 27.5%

methyl 3-((2-(benzyloxy)-2-oxoethyl)carbamoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-7-carboxylate

المردود 27.5%

المذيبات

H2O

DCM

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe layers were separated
2. 2
   استخلاصthe aqueous layer was extracted with DCM (3×)
3. 3
   غسيلthe organics were washed with H2O (2×)
4. 4
   تجفيفdried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىto yield a yellow solid

الإجراء التجريبي

4-hydroxy-7-(methoxycarbonyl)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (107 mg, 386 μmol), glycine benzyl ester hydrochloride (117 mg, 579 μmol), pybop (603 mg, 1158 μmol), and diisopropylethylamine (403 μl, 2316 μmol) were dissolved in DMF and stirred at room temperature for 24 hours. The reaction mixture was diluted with H2O and DCM, the layers were separated and the aqueous layer was extracted with DCM (3×), the organics were washed with H2O (2×) and dried over MgSO4, filtered and concentrated to yield a yellow solid. Flash column chromatography was performed using 2:1 Hex/EtOAc to give 45 mg of desired product.

المصدر