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

Triethylamine → 4-{[N-((1R)-1-Carbamoyl-3 methyl-butyl)-N-(4-chlorobenzenesulfonyl)amino]-methyl}-piperidine-1-carboxylic acid phenethylamide

HRID 1594208
노트
인쇄 미리보기

반응식

HRID 1594208 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20]([NH2:22])=[O:21])[CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.[N:34]([CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[C:35]=[O:36].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:37]([NH:34][C:35]([N:16]1[CH2:15][CH2:14][CH:13]([CH2:12][N:11]([C@@H:19]([C:20](=[O:21])[NH2:22])[CH2:23][CH:24]([CH3:26])[CH3:25])[S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])[CH2:18][CH2:17]1)=[O:36])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 160602Phenethyl isocyanateHCID 516892Sodium BicarbonateHCID 59001103(2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(piperidin-4-ylmethyl)amino]-4-methyl-pentanoic acid amide

생성물 1

HCID 590010804-{[N-((1R)-1-Carbamoyl-3 methyl-butyl)-N-(4-chlorobenzenesulfonyl)amino]-methyl}-piperidine-1-carboxylic acid phenethylamide수율 55.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2R)-2-[N-(4-chlorobenzenesulfonyl)-N-(piperidin-4-ylmethyl)amino]-4-methyl-pentanoic acid amide (Example 126, 0.10 g, 0.22 mmol) and Et3N (32 μL, 0.25 mmol) in CH2Cl2 (3.0 mL) was added (2-isocyanato-ethyl)-benzene (0.040 mL, 0.30 mmol). The reaction was stirred at rt for 18 h and then was poured into sat. aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated to an oily residue. The residue was further purified on a Biotage system (eluted with 75% EtOAc/hexanes) to afford the desired product as a white solid (67 mg, 52%). MS(ESI), (M+H)+549.00; 1H NMR (CDCl3, 500 MHz) δ7.71 (d, 2H, J=8.6), 7.71 (d, 2H, J=8.9), 7.15-7.35 (m, 5H), 6.64 (s, 1H), 5.86 (s, 1H), 4.15 (dd, 1H, J=5.2, 9.5), 3.88 (d, 1H, J=13), 3.76 (d, 1H, J=13), 3.46 (t, 2H, J=6.7), 3.21-3.29 (m, 1H), 2.97 (dd, 1H, J=4.6, 14), 2.65-2.85 (m, 4H), 1.75-1.95 (m, 3H), 1.00-1.30 (m, 5H), 0.75-0.80 (m, 1H), 0.72 (d, 3H, J=6.7), 0.67 (d, 3H, J=6.7).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oily residue
  5. customThe residue was further purified on a Biotage system (eluted with 75% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-f33212f38d0e415e9f7ce9c2f0087fbb
출처 데이터셋
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07300936B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트