Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Triphenylphosphine → 5-bromo-3-[2(R)-tert-butoxycarbonylamino-2-cyclohexylethyl]-1-[2,6-difluorobenzyl]-6-methyl-pyrimidine-2,4(1H,3H)-dione
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Triphenylphosphine | HCID 11776 | — |
| 반응물 | Di-tert-butyl diazene-1,2-dicarboxylate | HCID 6034084 | — |
| 반응물 | 5-Bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione | HCID 12094518 | — |
| 반응물 | Tert-butyl N-(1-cyclohexyl-2-hydroxyethyl)carbamate | HCID 22037861 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | 5-bromo-3-[2(R)-tert-butoxycarbonylamino-2-cyclohexylethyl]-1-[2,6-difluorobenzyl]-6-methyl-pyrimidine-2,4(1H,3H)-dione | HCID 21018402 | 95.4% |
반응 단계
A solution of tert-butyl 1-cyclohexyl-2-hydroxyethylcarbamate 11a (638 mg, 2.62 mmol) in THF (10 mL) was treated with 5-bromo-1-(2,6-difluorobenzyl)-6-methylpyrimidine-2,4(1H,3H)-dione 4d.1 (869 mg, 2.62 mmol) and triphenylphosphine (1.03 g, 3.93 mmol) at ambient temperature, then di-tert-butylazodicarboxylate (906 mg, 3.93 mmol) was introduced. The reaction mixture was stirred at ambient temperature for 16 hours and volatiles were evaporated. The residue was partitioned between saturated NaHCO3/H2O and EtOAc. The organic layer was dried (sodium sulfate), evaporated, and purified by flash chromatography (silica, 25% EtOAc/hexanes) to give compound 11b (1.39 g, 95.4%). MS (CI) m/z 456.1, 458.1 (MH+-Boc).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07229995B2 |
| 출처 데이터셋 | uspto-grants-2007_06 |
| ORD ID | ord-fb8ca64f6c62432498ebe12ff8e512f4 |
| 출처 메모 | uspto-grants-2007_06 |