Triethylamine → 2-(4-(Tert-butoxycarbonyl)-1-(4,5-dichloro-2-nitrophenyl)piperazin-2-yl)acetic acid

HRID 80497

반응식

HRID 80497 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][C:3]=1[Cl:12].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C)C=O.O>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:5]2[CH:4]=[C:3]([Cl:12])[C:2]([Cl:1])=[CH:7][C:6]=2[N+:8]([O-:10])=[O:9])[CH:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 5339511,2-Dichloro-4-fluoro-5-nitrobenzeneHCID 446077242-(4-(tert-Butoxycarbonyl)piperazin-2-yl)acetic acid

생성물 1

HCID 672493902-(4-(Tert-butoxycarbonyl)-1-(4,5-dichloro-2-nitrophenyl)piperazin-2-yl)acetic acid

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

1,2-Dichloro-4-fluoro-5-nitrobenzene (0.125 mL, 0.952 mmol) and 2-(4-(tert-butoxycarbonyl)piperazin-2-yl)acetic acid (256 mg, 1.048 mmol) were dissolved in N,N-dimethylformamide (2 mL) and water (1 mL). Triethylamine (0.398 mL, 2.86 mmol) was slowly added. The resulting mixture was heated at 50° C. overnight. The mixture was concentrated and ethyl acetate was added. 1N HCl was then added slowly until the pH=6. The water layer was separated and washed multiple times with ethyl acetate. The organic layers were then combined and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of 10% to 50% of ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.32 (br, 1H), 8.17 (s, 1H), 7.69 (s, 1H), 3.36-3.90 (m, 4H), 2.97-3.29 (m, 2H), 2.88 (dd, J=8.92, 3.37 Hz, 1H), 2.18-2.47 (m, 2H), 1.41 (s, 9H); MS (DCI+) m/z 434.1 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated
  2. additionethyl acetate was added
  3. addition1N HCl was then added slowly until the pH=6
  4. customThe water layer was separated
  5. washwashed multiple times with ethyl acetate
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with a gradient of 10% to 50% of ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-cabe02fd5ee342638092bf6c4cf753a8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846663B2

연결된 노트

불러오는 중…