반응 #426414

반응 방정식

(S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

(S)-methyl 3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

EDC

HOAt

NMM

→

title compound

수율 100.2%

(S)-Methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

수율 100.2%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타The resulting reaction mixture
2. 2
   기타quenched with EtOAc and sat. NaHCO3
3. 3
   추출The aqueous layer was extracted with EtOAc (3×)
4. 4
   세척The combined organic extracts were washed with 1N HCl (2×), sat. aq. NaCl solution (1×)
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo

실험 절차

To a 0° C. solution of (S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid (473 mg, 2.04 mmol) and (S)-methyl 3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate (745 mg, 2.04 mmol) in CH2Cl2 (12.4 mL) was added EDC (471 mg, 2.45 mmol), HOAt (334 mg, 2.45 mmol) and NMM (675 μL, 6.14 mmol). The resulting reaction mixture was allowed to warm to room temperature overnight and then quenched with EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (3×). The combined organic extracts were washed with 1N HCl (2×), sat. aq. NaCl solution (1×), dried over MgSO4, filtered and concentrated in vacuo to give the title compound (1.18 g, 2.045 mmol, 100%) as a light yellow foam, which was used without further purification. MS (ESI+) m/z 578.2 (M+H)+.

출처