Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → 5(S)-[1(S)-(Boc-amino)-2-(p-benzyloxyphenyl)-ethyl]-3(R)-(p-benzyloxyphenylmethyl)-dihydrofuran-2-(3H)-one
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | 2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- | HCID 81646 | — |
| 반응물 | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| 반응물 | p-Benzyloxybenzyl iodide | HCID 11723738 | — |
| 반응물 | [(S)-2-(4-Benzyloxy-phenyl)-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester | HCID 54401688 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | 5(S)-[1(S)-(Boc-amino)-2-(p-benzyloxyphenyl)-ethyl]-3(R)-(p-benzyloxyphenylmethyl)-dihydrofuran-2-(3H)-one | HCID 15659560 | — |
반응 단계
Analogously to Example 21 D) 1)c), 2.47 g (6.0 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-benzyloxyphenyl)ethyl]-dihydrofuran-2-(3H)-one (Example 46 c)) dissolved in 12 ml of THF and 1.2 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone are deprotonated at -70° C. with 11.73 ml of lithium bis(trimethylsilyl)amide 1M in THF and alkylated (60 min) with 1.946 g (6.0 mmol) of p-benzyloxybenzyl iodide (Example 44a)) in 3 ml of THF. Column chromatography (SiO2, hexane/ethyl acetate 4:1) and crystallisation from ethyl acetate/hexane yields the pure title compound: TLC Rf (D)=0.45; tRet (I)=19.9 min; FAB-MS (M+H)+ =608.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US05643878 |
| 출처 데이터셋 | uspto-grants-1997_07 |
| ORD ID | ord-d712656313174fa891581520ea0c5fbc |
| 출처 메모 | uspto-grants-1997_07 |