Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate → tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl)-4-morpholinecarboxylate
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate | HCID 981230 | — |
| 반응물 | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| 반응물 | 3-Tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl bromide | HCID 18352495 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl)-4-morpholinecarboxylate | HCID 57296200 | 71.3% |
반응 단계
According to example 142, 3.82 g of tert-butyl (2R, 3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate was alkylated with 3.86 g of 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl bromide in 80 mL of anhydrous THF using 11.34 mL of 1 M sodium bis(trimethylsilyl)amide in THF. The crude product was subjected to flash chromatography on silica gel (85:15 hexane:EtOAc) to afford 4.85 g (71%) of tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl)-4-morpholinecarboxylate as a white foam, m.p. 75-83° C.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US06140100 |
| 출처 데이터셋 | uspto-grants-2000_10 |
| ORD ID | ord-4cf691fcca5d4b6e8b8446acc3212b0b |
| 출처 메모 | uspto-grants-2000_10 |