1-Hydroxybenzotriazole → (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(S)-2-acetyloxy-2-phenylacetyl]perhydroisoindol-4-ol

HRID 2211415ノート

反応式

HRID 2211415 の反応式
ON1C2C=CC=CC=2N=N1.[C:11]([O:14][C@@H:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([OH:18])=O)(=[O:13])[CH3:12].Cl.[C:26]1([C:32]2([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C@@H:40]3[C@@H:36]([CH2:37][NH:38][CH2:39]3)[C@@:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[O:48][CH3:49])([OH:41])[CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:50]1([C:32]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:40]3[C@@H:36]([CH2:37][N:38]([C:16](=[O:18])[C@@H:15]([O:14][C:11](=[O:13])[CH3:12])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:39]3)[C@@:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[O:48][CH3:49])([OH:41])[CH2:34][CH2:33]2)[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6923379(+)-O-Acetyl-L-mandelic AcidHCID 70218598(3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride

生成物 1

HCID 22858344(3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(S)-2-acetyloxy-2-phenylacetyl]perhydroisoindol-4-ol収率 98.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒4 回

実験手順

0.024 g of 1-hydroxybenzotriazole and 0.33 g of (S)-2-acetyloxy-2-phenylacetic acid are added to a suspension of 0.75 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-perhydroisoindol-4-ol hydrochloride in 60 cm3 of dry methylene chloride, this solution is then cooled to +5° C. and a suspension of 0.4 g of 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride in 20 cm3 of dry methylene chloride is rapidly added, followed by a solution of 0.63 cm3 of diisopropylethylamine in 20 cm3 of dry methylene chloride. The reaction mixture is stirred at +5° C. for 2 hours and at room temperature for 24 hours, diluted with 120 cm3 of methylene chloride, washed with 100 cm3 of water 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 2.5 cm, height 39 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (50/50 by volume) and collecting fractions of 60 cm3. Fractions 6 to 10 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). 0.96 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[2-acetyloxy-2-phenyl-(S)-acetyl]-perhydroisoindol-4-ol are obtained in the form of a white foam.

後処理

  1. temperaturethis solution is then cooled to +5° C.
  2. additionis rapidly added
  3. washwashed with 100 cm3 of water
  4. dry with materialwith 100 cm3 of an aqueous saturated solution of sodium chloride, dried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2.5 cm, height 39 cm)
  7. washby eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (50/50 by volume)
  8. customcollecting fractions of 60 cm3
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

出典と根拠

ORDレコード
ord-781e201ddc5f4bfd9c567bfb7509afa2
出典データセット
uspto-grants-1995_10
特許番号
US05463077

反応ノート

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