반응 #59272

반응 방정식

2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid

1-hydroxybenzotriazole

N-ethyldiisopropylamine

EDC

((S)-7-Amino-6-oxo-6,7-dihydro-dibenzo[b,d]azepin-5-yl)-acetic acid methyl ester

→

product

수율 70.0%

{(S)-6-Oxo-7-[2-(2,2,3,3,3-pentafluoro-propylcarbamoyl)-propionylamino]-6,7-dihydro-dibenzo[b,d]azepin-5-yl}-acetic acid methyl ester

수율 70.0%

용매

THF

반응 조건

후처리

1. 1
   기타the reaction mixture is quenched with water
2. 2
   추출extracted with ethyl acetate
3. 3
   추출The aqueous phase is extracted twice with ethyl acetate
4. 4
   추출the combined organic layers are extracted with water (2×5 ml) and saturated aqueous sodium chloride (5 ml)
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타evaporated to dryness

실험 절차

((S)-7-Amino-6-oxo-6,7-dihydro-dibenzo[b,d]azepin-5-yl)-acetic acid methyl ester (25 mg, 0.85 mmol) were dissolved in THF and subsequently treated with 2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid (25 mg, 0.1 mmol), 1-hydroxybenzotriazole (11.6 mg, 0.85 mmol), N-ethyldiisopropylamine (0.03 ml, 0.17 mmol) and EDC (16.5 mg, 0.85 mmol). After stirring for 2.5 h at ambient temperature, the reaction mixture is quenched with water and extracted with ethyl acetate. The aqueous phase is extracted twice with ethyl acetate and the combined organic layers are extracted with water (2×5 ml) and saturated aqueous sodium chloride (5 ml), combined, dried over anhydrous sodium sulfate and evaporated to dryness. Chromatography (silica, eluent cyclohexane/ethyl acetate 65/35) afforded the product as colorless solid (70%). MS: m/e=528 (M+H+).

출처