홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Tetrahydrofuran → Ethyl 2-(2-(tert-butoxycarbonylamino)pyridin-4-yl)propanoate

HRID 2069058
노트
인쇄 미리보기

반응식

HRID 2069058 반응식
Cl[C:2]1[CH:7]=[C:6]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1.C([NH:19][C:20](=[O:22])[O-:21])(C)(C)C.[C:23](=O)([O-])[O-].[Cs+].[Cs+].[CH2:29]1[CH2:33]OC[CH2:30]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[C:29]([O:21][C:20]([NH:19][C:2]1[CH:7]=[C:6]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1)=[O:22])([CH3:30])([CH3:33])[CH3:23]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 21252905Tert-butylcarbamateHCID 58532560Ethyl 2-(2-chloropyridin-4-yl)propanoate

생성물 1

HCID 58532575Ethyl 2-(2-(tert-butoxycarbonylamino)pyridin-4-yl)propanoate수율 61%

시약·촉매·용매 2

HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
65 °C

실험 절차

A mixture of ethyl 2-(2-chloropyridin-4-yl)propanoate (51) (1.55 g, 7.25 mmol), tert-butylcarbamate (2.55 g, 21.76 mmol), Pd2 dba3 (0.166 g, 0.181 mmol), caesium carbonate (3.55 g, 10.88 mmol) and Xantphos (0.210 g, 0.363 mmol) in THF (10 mL) was purged with nitrogen and heated at 65° C. for 48 hr. The mixture was then cooled to RT, diluted with water and extracted with ether. The ether layer was washed with water and brine and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 100 g, 5-10% EtOAc in isohexane, gradient elution) to afford the title compound (52) (1.35 g, 61%): m/z 295 (M+H)+ (ES+).

후처리

  1. customwas purged with nitrogen
  2. temperatureThe mixture was then cooled to RT
  3. additiondiluted with water
  4. extractionextracted with ether
  5. washThe ether layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (SiO2, 100 g, 5-10% EtOAc in isohexane, gradient elution)

출처 및 근거

ORD 기록
ord-663ab8ce6d8147fdbdd8d3baf21496f6
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08299073B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트