Indole-3-Acetic Acid → (3aRS,4RS,5RS,7aRS)-7,7-dimethyl-4-(2-methoxyphenyl)-2-[(3-indolyl)acetyl]-4,5-perhydroisoindolediol

HRID 55413

反応式

HRID 55413 の反応式
[CH3:1][C:2]1([CH3:21])[CH:10]2[CH:6]([CH2:7][NH:8][CH2:9]2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])([OH:11])[CH:4]([OH:20])[CH2:3]1.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH2:31][C:32](O)=[O:33])=[CH:23]1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>ClCCl.ON1C2C=CC=CC=2N=N1>[CH3:1][C:2]1([CH3:21])[CH:10]2[CH:6]([CH2:7][N:8]([C:32](=[O:33])[CH2:31][C:24]3[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[NH:22][CH:23]=3)[CH2:9]2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])([OH:11])[CH:4]([OH:20])[CH2:3]1

参加物

7

反応物 4

HCID 802Indole-3-Acetic AcidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67714248HCID 67714248、化合物

生成物 1

HCID 67714307(3aRS,4RS,5RS,7aRS)-7,7-dimethyl-4-(2-methoxyphenyl)-2-[(3-indolyl)acetyl]-4,5-perhydroisoindolediol収率 70.9%

試薬・触媒・溶媒 2

HCID 757711-Hydroxybenzotriazole触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 0.44 g of (3aRS,4RS,5RS,7aRS)-7,7-dimethyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol and 0.29 g of 3-indoleacetic acid in 40 cm3 of dichloromethane, cooled to 0° C., are added 5 mg of 1-hydroxybenzotriazole, 0.35 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.42 cm3 of diisopropylethylamine. The mixture is stirred for 15 hours at room temperature, 100 cm3 of dichloromethane are added and the organic phase is washed with 50 cm3 of aqueous sodium bicarbonate solution and with 60 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The cream-coloured foam obtained is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 1 cm, height 30 cm), eluting under a pressure of 0.5 bar nitrogen with a mixture of dichloromethane and methanol (97/3 by volume) and collecting 30 cm3 fractions. Fractions 5 to 7 are combined and then concentrated to dryness under reduced pressure (2.7 kPa); the solid obtained is recrystallized in 5 cm3 of isopropyl ether. 0.48 g of (3aRS,4RS,5RS,7aRS)-7,7-dimethyl-4-(2-methoxyphenyl)-2-[(3-indolyl)acetyl]-4,5-perhydroisoindolediol is obtained, melting at 160-165° C.

後処理

  1. washthe organic phase is washed with 50 cm3 of aqueous sodium bicarbonate solution and with 60 cm3 of saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe cream-coloured foam obtained
  5. customis chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 1 cm, height 30 cm)
  6. washeluting under a pressure of 0.5 bar nitrogen with a mixture of dichloromethane and methanol (97/3 by volume)
  7. customcollecting 30 cm3 fractions
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  9. customthe solid obtained
  10. customis recrystallized in 5 cm3 of isopropyl ether

出典と根拠

ORDレコード
ord-24a7bbc173db4cbf925fd9aed2374da0
出典データセット
uspto-grants-1997_04
特許番号
US05624950

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