Sodium Chloride → Perhydroisoindole-4,5-diol

HRID 375447노트

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HRID 375447 반응식
O.[OH:2]N1C2C=CC=CC=2N=N1.CN(C)[CH2:14][CH2:15][CH2:16][N:17]=[C:18]=NCC.C(N(C(C)C)CC)(C)C.C[O:33][C:34]1C=C[CH:37]=[CH:36][C:35]=1[C@H](C)C(O)=O.[Cl-].[Na+]>ClCCl.O>[CH2:16]1[CH:15]2[CH:14]([CH:34]([OH:33])[CH:35]([OH:2])[CH2:36][CH2:37]2)[CH2:18][NH:17]1

참가 물질

8

반응물 5

HCID 5234Sodium ChlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 11137716(S)-2-(2-Methoxyphenyl)propanoic acid

생성물 1

HCID 18994337Perhydroisoindole-4,5-diol

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

30 mg of 1-hydroxybenzotriazole hydrate, 0.66 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 0.6 cm3 of diisopropylethylamine are added to a solution of 1.1 g of (3AS,4S,5S,7AS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindole-4,5-diol and 0.58 g of (S)-2-(2-methoxyphenyl)propanoic acid in 30 cm3 of dichloromethane, cooled to 0° C. The mixture is stirred at room temperature for 3 hours and 30 minutes and 100 cm3 of water and 50 cm3 of an aqueous saturated solution of sodium chloride are added. The organic phase is decanted, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The yellow residue obtained is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 30 cm) by eluting under a nitrogen pressure of 50 kPa with a mixture of cyclohexane and ethyl acetate (60/40 by volume) and collecting fractions of 25 cm3. Fractions 6 to 14 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). 0.9 g of (3AS,4S,5S,7AS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[S)- 2-(2methoxyphenyl)propionyl]perhydroisoindole-4,5-diol which melts at 256° C. is obtained.

후처리

  1. customThe organic phase is decanted
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe yellow residue obtained
  5. customis chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 30 cm)
  6. washby eluting under a nitrogen pressure of 50 kPa
  7. additionwith a mixture of cyclohexane and ethyl acetate (60/40 by volume)
  8. customcollecting fractions of 25 cm3
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

출처 및 근거

ORD 기록
ord-6886ebf148784daba51a68de0b2d68d1
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05484804

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