Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Pyrrole-2-Carboxylic Acid → (7S,10S,13S)-10-Isopropyl-9,12-dioxo-13-[(1H-pyrrole-2-carbonyl)-amino]-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Pyrrole-2-Carboxylic Acid | HCID 12473 | — |
| 반응물 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 반응물 | Diisopropylethylamine | HCID 81531 | — |
| 반응물 | (7S,10S,13S)-13-Amino-10-isopropyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1-(18),15(19),16-triene-7-carboxylic acid methyl ester hydrogen chloride salt | HCID 86650244 | — |
| 용매 | 1,2-Dichloroethane | HCID 11 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | (7S,10S,13S)-10-Isopropyl-9,12-dioxo-13-[(1H-pyrrole-2-carbonyl)-amino]-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester | HCID 66846964 | — |
반응 단계
Amine 47 (0.37 g) was dissolved in anhydrous DMF (5 mL). 1H-pyrrole-carboxylic acid (0.11 g), DIPEA (0.72 mL), EDC (0.25 g) and HOBt (0.2 g) were added and the reaction mixture was stirred at rt for 18 h before being partitioned between chloroform and 1M hydrochloric acid. The aqueous phase was extracted three more times with chloroform and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 20% EtOAc/(50/70) petroleum ether to EtOAc to yield an off-white solid, 279 mg, 55%. Rf=0.15. (20% EtOAc/(50/70) petroleum ether).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US09434762B2 |
| 출처 데이터셋 | uspto-grants-2016_09 |
| ORD ID | ord-01ec85a685a64f97889bf9e080a77bb0 |
| 출처 메모 | uspto-grants-2016_09 |