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

Water → ethyl (6-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate

HRID 1792931
노트
인쇄 미리보기

반응식

HRID 1792931 반응식
[H-].[Na+].[F:3][C:4]([F:21])([F:20])[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH:8]2O.[F:22][C:23]([F:40])([F:39])[C:24]1[CH:32]=[C:31]2[C:27]([CH:28](O)[N:29]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:30]2=[O:33])=[CH:26][CH:25]=1.O.C[O:43][CH2:44][CH2:45]OC>>[F:3][C:4]([F:21])([F:20])[C:5]1[CH:6]=[C:7]2[C:11]([C:10](=[O:14])[N:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH:8]2[CH2:45][C:44]([O:33][CH2:30][CH3:31])=[O:43])=[CH:12][CH:13]=1.[F:22][C:23]([F:40])([F:39])[C:24]1[CH:32]=[C:31]2[C:27](=[CH:26][CH:25]=1)[CH:28]([CH2:45][C:44]([O:14][CH2:10][CH3:11])=[O:43])[N:29]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:30]2=[O:33]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 22025449HCID 22025449, 화합물HCID 22025460HCID 22025460, 화합물

생성물 2

HCID 86591365ethyl (6-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate
HCID 86591366
ethyl (5-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate

반응 조건

온도
20 °C

실험 절차

Ethyl (5-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate and ethyl (6-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate are prepared as described in Example 2, starting with 1.32 g of 60% sodium hydride in 120 cm3 of 1,2-dimethoxyethane, 6.57 cm3 of triethyl phosphonoacetate and 12.07 g of 5-trifluoromethyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-trifluoromethyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one. The mixture is refluxed for 24 hours and then cooled to a temperature in the region of 20° C. The reaction mixture is then treated with 150 cm3 of water and the mixture is then extracted with 3 times 250 cm3 of diethyl ether. The organic extracts are combined, washed with 150 cm3 of saturated brine, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. A mixture of 2.3 g of the residue is injected onto a column 8 cm in diameter containing 1.2 kg of Whelk OI,SS chiral stationary phase. The elution is performed with a mobile phase composed of a mixture of dichloromethane, ethanol and heptane in proportions of 14.5/0.5/85 v/v. Two additional injections of 2.7 g and 3 g are made under identical conditions. The fractions comprising the first regioisomer are combined and concentrated to dryness under reduced pressure (1 kPa) at a temperature in the region of 40° C. 1.86 g of ethyl (5-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate are thus obtained in the form of a white solid (Rf=0.64, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)). The fractions comprising the second regioisomer are combined and concentrated to dryness under reduced pressure (1 kPa) at a temperature in the region of 40° C. to give 2.79 g of a white solid. This product is repurified by chromatography under argon pressure (80 kPa) on a cartridge of silica gel (particle size 32-63 μm), eluting with a mixture of cyclohexane/ethyl acetate (90/10 by volume). The fractions comprising the expected product are combined and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.25 g of ethyl (6-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate are thus obtained in the form of a colorless viscous oil. (Rf=0.46, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (75/25 by volume)).

후처리

  1. temperatureThe mixture is refluxed for 24 hours
  2. extractionthe mixture is then extracted with 3 times 250 cm3 of diethyl ether
  3. washwashed with 150 cm3 of saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  7. additionA mixture of 2.3 g of the residue
  8. additioncontaining 1.2 kg of Whelk OI,SS chiral stationary phase
  9. washThe elution
  10. additioncomposed of a mixture of dichloromethane, ethanol and heptane in proportions of 14.5/0.5/85 v/v
  11. concentrationconcentrated to dryness under reduced pressure (1 kPa) at a temperature in the region of 40° C

출처 및 근거

ORD 기록
ord-b911b6e30eac40c5be3c86438d8fe792
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07078428B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트