Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
1-Hydroxybenzotriazole → {(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidine-1-yl]-ethyl}-carbamic acid tert-butyl ester
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 반응물 | Diisopropylethylamine | HCID 81531 | — |
| 반응물 | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| 반응물 | N-(tert-Butoxycarbonyl)-L-cyclohexylglycine | HCID 7004938 | — |
| 반응물 | (S)-2-(3-phenoxy-phenyl)-pyrrolidine | HCID 59787976 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 용매 | Sodium chloride; water | HCID 57417360 | — |
| 생성물 | {(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidine-1-yl]-ethyl}-carbamic acid tert-butyl ester | HCID 59787985 | — |
반응 단계
(S)-2-(3-phenoxy-phenyl)-pyrrolidine (1.2 g, 5.02 mmol) is added to a solution of Boc-L-α-cyclohexylglycine (1.42 g, 5.2 mmol), HOBt (1.0 g, 7.53 mmol) and HBTU (2.86 g, 7.53 mmol) in 10 mL of DMF. Hunig's base (3.6 Ml, 20 mmol) is added and the mixture is stirred for 30 minutes. The mixture is diluted with brine (20 mL) and extracted with EtOAc (3×10 mL). The organics were combined, dried over Na2SO4, filtered, concentrated under reduced pressures and purified by silica gel column chromatography (20% EtOAc/Hexanes) to give {(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidine-1-yl]-ethyl}-cabamic acid tert-butyl ester as a white powder (1.65 g, 66%). LCMS m/z 479.2 (M+1).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07419975B2 |
| 출처 데이터셋 | uspto-grants-2008_09 |
| ORD ID | ord-154725067da14020b8e904cedf309387 |
| 출처 메모 | uspto-grants-2008_09 |