반응 #502127

반응 방정식

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

tert-butyl N-(2-hydroxyethyl)carbamate

1,3-dicyclohexylcarbodiimide

→

title compound

수율 82.4%

2-((tert-Butoxy)carbonylamino)ethyl(2S)-2-(6-methoxy(2-naphthyl))propanoate

수율 82.4%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타The byproduct, dicyclohexyl urea, was removed by filtration
2. 2
   농축The filtrate was concentrated
3. 3
   workup.DISSOLUTIONdissolved in EtOAc (50 mL)
4. 4
   온도cooled in a dry-ice bath
5. 5
   기타to precipitate the remaining dicyclohexyl urea
6. 6
   여과filtered
7. 7
   농축The filtrate was concentrated
8. 8
   workup.DISSOLUTIONdissolved in CH2Cl2 (15 mL)
9. 9
   기타precipitated
10. 10
    기타The solid was dried under vacuum

실험 절차

A solution of (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (naproxen, 7.60 g, 33.0 mmol), tert-butyl N-(2-hydroxyethyl)carbamate (5.30 g, 32.9 mmol), N,N-dimethylaminopyridine (DMAP, 0.35 g, 2.86 mmol) and 1,3-dicyclohexylcarbodiimide (6.80 g, 33.0 mmol) in CH2Cl2 (200 mL) was stirred at ambient temperature overnight. The byproduct, dicyclohexyl urea, was removed by filtration. The filtrate was concentrated, dissolved in EtOAc (50 mL) and then cooled in a dry-ice bath to precipitate the remaining dicyclohexyl urea and then filtered. The filtrate was concentrated, dissolved in CH2Cl2 (15 mL) and hexane (200 mL) and then stirred until the product precipitated. The solid was dried under vacuum to give the title compound (10.12 g, 82% yield). Mp 82-84° C. 1H NMR (300 MHz, CDCl3) δ 7.72-7.65 (m, 3H), 7.42-7.38 (m, 1H), 7.16-7.11 (m, 2H), 5.05 (br, 1H), 4.13 (t, J=5.3 Hz, 2H), 3.91 (s, 3H), 3.87 (q, J=7.1 Hz, 1H), 3.30 (br. q, 2H), 1.58 (d, J=7.1 Hz, 3H), 1.45 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 174.4, 157.6, 155.6, 135.4, 133.6, 129.2, 128.8, 127.1, 126.0, 125.8, 119.0, 105.5, 79.3, 63.7, 55.2, 45.2, 39.5, 28.2, 18.3. Mass spectrum (API-TIS) m/z 374 (MH)+. Anal. calcd. for C21H27NO5: C, 67.54; H, 7.29; N, 3.75. Found: C, 67.43; H, 7.16; N, 3.66.

출처