반응 #1453624

반응 방정식

(2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentenoic acid

EDC

N-methylallylamine

→

1,1-dimethylethyl {(1S)-1-[(2-propen-1-ylamino)carbonyl]-3-buten-1-yl}carbamate

수율 28.4%

반응 조건

후처리

1. 1
   기타before being quenched by the addition of 1 M HCl (15 mL)
2. 2
   기타The resulting biphasic mixture was separated
3. 3
   추출the aqueous phase was extracted once with DCM
4. 4
   건조The combined organics were dried over sodium sulfate
5. 5
   농축concentrated

실험 절차

To a stirred solution of (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentenoic acid (2.82 g, 13 mmol), DMAP (1.9 g, 16 mmol) and EDC (3.1 g, 16 mmol) was added N-methylallylamine (1.38 mL, 14 mmol). The reaction was stirred for 72 hours before being quenched by the addition of 1 M HCl (15 mL). The resulting biphasic mixture was separated and the aqueous phase was extracted once with DCM. The combined organics were dried over sodium sulfate and concentrated to yield 1,1-dimethylethyl {(1S)-1-[(2-propen-1-ylamino)carbonyl]-3-buten-1-yl}carbamate (0.94 g, 28%). LCMS: (M−tBut)+: 238.1.

출처