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

Diisopropylethylamine → {6-Chloro-3-methyl-4-[4-(2-trifluoromethyl-benzenesulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

HRID 1468455
노트
인쇄 미리보기

반응식

HRID 1468455 반응식
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:23])[CH:11]=2)[CH:6]=1.[F:25][C:26]([F:38])([F:37])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](Cl)(=[O:35])=[O:34].C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[C:26]([F:25])([F:37])[F:38])(=[O:35])=[O:34])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:23])[CH:11]=2)[CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 86694946[4-(4-Amino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

생성물 1

HCID 86695032{6-Chloro-3-methyl-4-[4-(2-trifluoromethyl-benzenesulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester수율 83.1%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of [4-(4-amino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (100 mg, 0.29 mmol) and 2-trifluoromethyl-benzenesulfonyl chloride (146 mg, 0.59 mmol) in THF (5.5 mL) was added diisopropylethylamine (0.15 mL, 0.85 mmol) at 0° C. under nitrogen. After addition, the reaction mixture was warmed to room temperature and stirred for 3 hours. The solvent was removed under vacuum and the residue was diluted with water (10 mL). Then, the organic compound was extracted into ethyl acetate (2×20 mL). The combined organic extracts were washed with brine solution (30 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum gave the crude residue which was purified by using an ISCO (40 g) column chromatography eluting with 5-30% ethyl acetate in hexanes to afford {6-chloro-3-methyl-4-[4-(2-trifluoromethyl-benzenesulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (132 mg, 82%) as a light yellow foam. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.80 (s, 1 H), 8.16 (d, J=7.2 Hz, 1 H), 8.03 (dd, J=7.2, 1.7 Hz, 1 H), 7.82-7.96 (m, 4 H), 7.45 (dd, J=8.8, 1.6 Hz, 1 H), 7.25 (d, J=8.5 Hz, 2 H), 7.12 (d, J=8.5 Hz, 2 H), 6.95 (d, J=1.6 Hz, 1 H), 3.92 (s, 2 H), 3.63 (s, 3 H), 1.98 (s, 3H). HRMS calcd. for C27H20ClF3NO4S [(M−H)−] 546.0759, obsd. 546.0762.

후처리

  1. additionAfter addition
  2. customThe solvent was removed under vacuum
  3. additionthe residue was diluted with water (10 mL)
  4. extractionThen, the organic compound was extracted into ethyl acetate (2×20 mL)
  5. washThe combined organic extracts were washed with brine solution (30 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationFiltration of the drying agent and concentration of the solvent under vacuum
  8. customgave the crude residue which
  9. customwas purified
  10. washeluting with 5-30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-a017ac72073c4d5192b96e377e11eb6f
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09000044B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트