Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
3-Fluorobenzyl bromide → 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(m-fluorophenylmethyl)-dihydrofuran-2-(3H)-one
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | 3-Fluorobenzyl bromide | HCID 68007 | — |
| 반응물 | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| 반응물 | tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate | HCID 10870461 | — |
| 반응물 | Ethyl acetate hexane | HCID 21226206 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(m-fluorophenylmethyl)-dihydrofuran-2-(3H)-one | HCID 67718720 | — |
반응 단계
Analogously to Example 21 D) 1)c), 5.0 g (16.37 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-dihydrofuran-2-(3H)-one [Example 21 D) 1)b)] dissolved in 75 ml of THF are deprotonated at -75° C. with 32.7 ml of lithium bis(trimethylsilyl)amide 1M in THF and alkylated starting at -75° C. with 3.4 g (18.0 mmol) of 3-fluorobenzyl bromide (Fluka; Buchs/Switzerland) (warming up during 60 min up to max. -50° C.). Column chromatography (SiO2, hexane/ethyl acetate 3:1) yields the title compound: TLC Rf (D)=0.6; tRet (I)=17.2 min.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US05643878 |
| 출처 데이터셋 | uspto-grants-1997_07 |
| ORD ID | ord-9f41d5bdadeb47a383a7f39bdcf9df1a |
| 출처 메모 | uspto-grants-1997_07 |