Sodium Azide → (3aRS,4RS,6SR,7aSR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol

HRID 1599156노트

반응식

HRID 1599156 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1([OH:44])[CH2:21][CH:20]([CH2:22]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:19][CH:18]2[CH:14]1[CH2:15][N:16]([C:33](=[O:43])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][CH3:42])[CH2:17]2>CN(C)C=O.O>[N:1]([CH2:22][CH:20]1[CH2:19][CH:18]2[CH:14]([CH2:15][N:16]([C:33](=[O:43])[CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])[CH2:17]2)[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH3:5])([OH:44])[CH2:21]1)=[N+:2]=[N-:3]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 86752423(3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-6-tosylmethylperhydroisoindol-4-ol

생성물 1

HCID 86752422(3aRS,4RS,6SR,7aSR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol수율 98.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

0.35 g of sodium azide is added to a solution of 2.03 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-6-tosylmethylperhydroisoindol-4-ol in 10 cm3 of dimethylformamide. The reaction mixture is heated at 50° C. for 8 hours and stirred at 20° C. for 48 hours and then diluted with 150 cm3 of water and subjected to extraction twice with 40 cm3 of ethyl acetate. The organic phase is washed with 50 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). 1.6 g of (3aRS,4RS,6SR,7aSR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol are obtained in the form of a thick white foam.

후처리

  1. extractionsubjected to extraction twice with 40 cm3 of ethyl acetate
  2. washThe organic phase is washed with 50 cm3 of water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

출처 및 근거

ORD 기록
ord-c1a950fb6ba94e648caed20f953e4756
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05739351

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