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

Dimethyl Sulfoxide → (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde

HRID 2186384
노트
인쇄 미리보기

반응식

HRID 2186384 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][C@@H:14]1[C@H:19]([CH2:20][CH2:21][CH:22]([OH:35])[C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17][N:16]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:15]1.C(N(CC)CC)C>ClCCl>[O:35]=[C:22]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1)[CH2:21][CH2:20][C@@H:19]1[CH2:18][CH2:17][N:16]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[CH2:15][C@@H:14]1[CH2:13][CH:12]=[O:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69353248(3R,4R)-3-(2-hydroxyethyl)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine

생성물 1

HCID 86758164(3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde수율 100.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매4회

실험 절차

A mixture of 13.7 g of dimethyl sulfoxide in 65 cm3 of dichloromethane was slowly added, with stirring and under an inert atmosphere, to a solution, cooled to a temperature in the region of −60° C., of 8.3 cm3 of oxalyl chloride in 65 cm3 of dichloromethane. After stirring the mixture for 15 minutes, 10 g of (3R,4R)-3-(2-hydroxyethyl)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine, dissolved in 65 cm3 of dichloromethane, were slowly added. After stirring the mixture for 30 minutes, 61.7 cm3 of triethylamine, dissolved in 65 cm3 of dichloromethane, were finally added dropwise. The mixture was stirred for a further 3 hours at approximately −60° C. and then poured onto 400 cm3 of ice-cold water. After separating the mixture by settling, the organic phase was washed with 400 cm3 of a 10% (by mass) aqueous citric acid solution and then dried over magnesium sulfate, filtered, and evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 9.95 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde were obtained in the form of an. oil with a brown color.

후처리

  1. additionwas slowly added
  2. stirringAfter stirring the mixture for 15 minutes
  3. additionwere slowly added
  4. stirringAfter stirring the mixture for 30 minutes
  5. additionwere finally added dropwise
  6. stirringThe mixture was stirred for a further 3 hours at approximately −60° C.
  7. customAfter separating the mixture
  8. washthe organic phase was washed with 400 cm3 of a 10% (by mass) aqueous citric acid solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C

출처 및 근거

ORD 기록
ord-ee99234dfd8844c2b160c69c4cf0bf66
출처 데이터셋
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06403610B1

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트