Diisopropylcarbodiimide → 6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic Acid Pentafluorophenyl Ester

HRID 1055785

반응식

HRID 1055785 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].C(N=C=NC(C)C)(C)C.[F:29][C:30]1[C:35](O)=[C:34]([F:37])[C:33]([F:38])=[C:32]([F:39])[C:31]=1[F:40]>ClCCl>[F:29][C:30]1[C:35]([O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])=[C:34]([F:37])[C:33]([F:38])=[C:32]([F:39])[C:31]=1[F:40]

참가 물질

5

반응물 3

HCID 12734DiisopropylcarbodiimideHCID 13041PentafluorophenolHCID 781851,3-Dihydro-1,3-dioxo-2H-isoindole-2-hexanoic acid

생성물 1

HCID 593472896-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic Acid Pentafluorophenyl Ester수율 101.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Referring to scheme 12, compound 41a (13.3 g, 51 mmol) was dissolved in anhydrous dichloromethane (40 mL) and cooled to 0° C. under argon. To the solution were added diisopropyl carbodiimide (6.31 g, 7.7 mL, 50 mmol) and pentafluoro phenol (42, 9.2 g, 50 mmol). After overnight the reaction mixture was evaporated to dryness. To the residue ethyl acetate (100 mL) was added and the filtered to remove diisopropyl urea. The precipitate was washed with ethyl acetate (50 mL). The combined organic layer was washed with saturated sodium bicarbonate and water. The organic layer was dried over sodium sulfate, filtered and evaporated to dryness. Compound 43a (Rf=0.8 in 10% EtOAc/Hexane, 21.65 g, 92%) was obtained, which was directly used for the next step without further purification.

후처리

  1. customAfter overnight the reaction mixture was evaporated to dryness
  2. additionTo the residue ethyl acetate (100 mL) was added
  3. filtrationthe filtered
  4. customto remove diisopropyl urea
  5. washThe precipitate was washed with ethyl acetate (50 mL)
  6. washThe combined organic layer was washed with saturated sodium bicarbonate and water
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

출처 및 근거

ORD 기록
ord-a7d17c5d571c48af99ee17648c0d0826
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394540B2

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