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2-Methoxyphenylacetic acid → HCID 15289540、化合物

HRID 2211416
ノート
印刷プレビュー

反応式

HRID 2211416 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][C:22]([OH:24])=O.Cl.[C:26]1([C@:32]2([OH:53])[CH2:40][CH2:39][C:38]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@@H:37]3[C@H:33]2[CH2:34][NH:35][CH2:36]3)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C(Cl)Cl>[C:26]1([C@:32]2([OH:53])[CH2:40][CH2:39][C:38]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C@@H:37]3[C@H:33]2[CH2:34][N:35]([C:22](=[O:24])[CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH3:13])[CH2:36]3)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 71342-Methoxyphenylacetic acidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 67736920HCID 67736920、化合物

生成物 1

HCID 15289540HCID 15289540、化合物収率 34.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒
3 回

実験手順

0.28 g of carbonyldiimidazole is added to a solution of 0.28 g of (2-methoxyphenyl)-acetic acid in 20 cm3 of dry methylene chloride. The mixture is stirred at room temperature for I hour and a suspension of 0.7 g of (3aS,4S,7aS)-4,7,7-triphenyl-perhydroisoindol-4-ol hydrochloride in 20 cm3 of dry methylene chloride and then 0.48 cm3 of triethylamine are subsequently added in succession. The reaction mixture is stirred at room temperature for 24 hours, diluted with 100 cm3 of methylene chloride, washed with 100 cm3 of water (twice) and then with 100 cm3 of an aqueous saturated solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 16 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (55/45 by volume) and collecting fractions of 20 cm3. Fractions 7 to 8 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallised in 16 cm3 of acetonitrile. The crystals are filtered off and dried. 0.3 g of (3aS,4S,7aS)-4,7,7-triphenyl-2-[(2-methoxyphenyl)-acetyl]-perhydroisoindol-4-ol is obtained in the form of white crystals which melt at 236° C.

後処理

  1. stirringThe reaction mixture is stirred at room temperature for 24 hours
  2. washwashed with 100 cm3 of water (twice) and then with 100 cm3 of an aqueous saturated solution of sodium chloride
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 16 cm)
  6. washby eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (55/45 by volume)
  7. customcollecting fractions of 20 cm3
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  9. customThe residue is crystallised in 16 cm3 of acetonitrile
  10. filtrationThe crystals are filtered off
  11. customdried

出典と根拠

ORDレコード
ord-e6ca78faf1154b9b82c33ec9afec4248
出典データセット
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05463077

反応ノート

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