تفاعل #502127

معادلة التفاعل

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

tert-butyl N-(2-hydroxyethyl)carbamate

1,3-dicyclohexylcarbodiimide

→

title compound

المردود 82.4%

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

المردود 82.4%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىThe byproduct, dicyclohexyl urea, was removed by filtration
2. 2
   تركيزThe filtrate was concentrated
3. 3
   workup.DISSOLUTIONdissolved in EtOAc (50 mL)
4. 4
   درجة الحرارةcooled in a dry-ice bath
5. 5
   أخرىto precipitate the remaining dicyclohexyl urea
6. 6
   ترشيحfiltered
7. 7
   تركيزThe filtrate was concentrated
8. 8
   workup.DISSOLUTIONdissolved in CH2Cl2 (15 mL)
9. 9
   أخرىprecipitated
10. 10
    أخرىThe solid was dried under vacuum

الإجراء التجريبي

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.

المصدر