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

HRID 1055785

反応式

HRID 1055785 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a7d17c5d571c48af99ee17648c0d0826
出典データセット
uspto-grants-2016_07
特許番号
US09394540B2

関連ノート

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