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

Isopropyl chloroformate → (2R)-2-(benzofuran-5-yl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N,N-dimethylethanamide

HRID 45625
노트
인쇄 미리보기

반응식

HRID 45625 반응식
C(O[C:6]([NH:8][C@H:9]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)[C:10]([OH:12])=O)=[O:7])(C)(C)C.CN1CCOCC1.C(OC(Cl)=O)(C)C.[O:36]1[C:40]2[CH:41]=[CH:42][C:43]([CH:45]([NH:51][C@H:52](C(O)=O)[CH2:53][CH:54]([CH3:56])[CH3:55])[C:46]([N:48]([CH3:50])[CH3:49])=[O:47])=[CH:44][C:39]=2[CH:38]=[CH:37]1>O1CCCC1.C1(C)C=CC=CC=1.CN(C)C=O>[O:36]1[C:40]2[CH:41]=[CH:42][C:43]([C@@H:45]([N:51]3[C@H:52]([CH2:53][CH:54]([CH3:56])[CH3:55])[C:6](=[O:7])[NH:8][C@H:9]([CH:13]4[CH2:14][C:15]5[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=5)[CH2:21]4)[C:10]3=[O:12])[C:46]([N:48]([CH3:49])[CH3:50])=[O:47])=[CH:44][C:39]=2[CH:38]=[CH:37]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 7917Isopropyl chloroformateHCID 79724-MethylmorpholineHCID 11208543(R)-2-((tert-Butoxycarbonyl)amino)-2-(2,3-dihydro-1H-inden-2-yl)acetic acidHCID 68847309N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucine

생성물 1

HCID 11477318(2R)-2-(benzofuran-5-yl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N,N-dimethylethanamide
수율 7.3%

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2R)-[(tert-butoxycarbonyl)amino](2,3-dihydro-1H-inden-2-yl)ethanoic acid (419 mg) in dry tetrahydrofuran (5 ml) at −20° C. under a nitrogen atmosphere was added N-methylmorpholine (158 μl) and a solution of isopropylchloroformate in toluene (1.0M, 1.44 ml). After 10 minutes, a solution of N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucine (478 mg) in dimethylformamide (5 ml) was added and the reaction was allowed to warm to room temperature. After 20 hours, the solvent was removed in vacuo and the residue was dissolved in 4N hydrochloric acid in dioxan (4 ml). After 4 hours methanol (13 ml) was added and the reaction was left to stand for a further 18 hours. The solvent was then removed in vacuo and the residue was separated between dichloromethane and saturated sodium bicarbonate solution. The organic phase was evaporated in vacuo and the residue was applied to an SPE (10 g, silica). The product was eluted using an ethyl acetate:methanol gradient (3:1 to 1:3) to afford (2R)-2-(benzofuran-5-yl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N,N-dimethylethanamide (51 mg).

후처리

  1. waitAfter 20 hours
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 4N hydrochloric acid in dioxan (4 ml)
  4. additionAfter 4 hours methanol (13 ml) was added
  5. waitthe reaction was left
  6. waitto stand for a further 18 hours
  7. customThe solvent was then removed in vacuo
  8. customthe residue was separated between dichloromethane and saturated sodium bicarbonate solution
  9. customThe organic phase was evaporated in vacuo
  10. washThe product was eluted

출처 및 근거

ORD 기록
ord-5b1a3e6d73e941e6861b9848f689eac2
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541579B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트