Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(p-benzyloxyphenyl)methyl]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 | tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate | HCID 10870461 | — |
| 반응물 | p-Benzyloxybenzyl iodide | HCID 11723738 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 용매 | Ethyl acetate hexane | HCID 21226206 | — |
| 생성물 | 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(p-benzyloxyphenyl)methyl]dihydrofuran-2-(3H)-one | HCID 15659556 | — |
반응 단계
Analogously to Example 21 D) 1)c), 1.13 g (3.70 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-dihydrofuran-2-(3H)-one [Example 21 D) 1)b)] dissolved in 4.8 ml of THF and 0.75 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone are deprotonated at -75° C. with 7.25 ml of lithium bis(trimethylsilyl)amide 1M in THF, and alkylated (15 min) with 1.2 g (3.7 mmol) of p-benzyloxybenzyl iodide in 2 ml of THF. Column chromatography (SiO2, hexane/ethyl acetate 2:1) yields the pure title compound: TLC Rf (D)=0.30; tRet (II)=28.2 min; FAB-MS (M+H)+ =502.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US05643878 |
| 출처 데이터셋 | uspto-grants-1997_07 |
| ORD ID | ord-374c252327f740d980ab7a5a84e043d0 |
| 출처 메모 | uspto-grants-1997_07 |