반응 #83394

반응 방정식

L-Pyroglutamic acid methyl ester

NaH

p-Cyanobenzylbromide

→

N-(4-Cyanobenzyl)-L-pyroglutamic acid methyl ester

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITthe mixture left
3. 3
   기타After 48 h the reaction mixture was partitioned between EtOAc and satd NaHCO3 solution
4. 4
   기타the aqueous layer separated
5. 5
   세척washed with CH2Cl2
6. 6
   세척washed with brine
7. 7
   건조dried (MgSO4)
8. 8
   여과Filtration and concentration to dryness
9. 9
   기타gave the white solid product

실험 절차

L-Pyroglutamic acid methyl ester (1.36 g, 0.0095 mol) was dissolved in dry THF (20 mL) under Ar, treated with NaH (60% oil dispersion) (0.58 g, 0.0145 mol) with stirring for 5 min, then the mixture was cooled to 0° C. p-Cyanobenzylbromide (1.78 g, 0.0091 mol) was added, and the mixture left to slowly warm to ambient temperature. After 48 h the reaction mixture was partitioned between EtOAc and satd NaHCO3 solution, the aqueous layer separated and washed with CH2Cl2, the organics combined, washed with brine and dried (MgSO4). Filtration and concentration to dryness followed by trituration with ether gave the white solid product. 1H NMR(CDCl3, 400 MHz) δ 7.62(2H, d, J=8 Hz), 7.33(2H, d, J=8 Hz), 4.98(1H, d, J=15.4 Hz), 4.13(1H, d, J=15.4 Hz), 3.99(1H, dd, J=3, 9 Hz) and 2.5-2.6 (1H, m), 2.4-2.5 (1H, m), 2.2-2.45 (1H, m), 2.1-2.2 (1H, m) ppm.

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