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Sodium Azide → (3aS,4S,6R,7aR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol

HRID 1599155
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HRID 1599155 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:46])[CH2:21][C@H:20]([CH2:22]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:19][C@@H:18]2[C@H:14]1[CH2:15][N:16]([C:34](=[O:45])[C@H:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[O:43][CH3:44])[CH3:36])[CH2:17]2>CN(C)C=O.O>[N:1]([CH2:22][C@@H:20]1[CH2:19][C@@H:18]2[C@@H:14]([CH2:15][N:16]([C:34](=[O:45])[C@H:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])[CH3:36])[CH2:17]2)[C@@:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH3:5])([OH:46])[CH2:21]1)=[N+:2]=[N-:3]
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참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 22884866(3aS,4S,6R,7aR)-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]-6-tosyloxymethyl perhydroisoindol-4-ol

생성물 1

HCID 86752421(3aS,4S,6R,7aR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol수율 99.4%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

반응 조건

온도
20 °C

실험 절차

1.68 g of sodium azide are added to a solution, which has been brought to 50° C., of 9.0 g (3aS,4S,6R,7aR)-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]-6-tosyloxymethylperhydroisoindol-4-ol in 50 cm3 of dimethylformamide. The reaction mixture is stirred at 20° C. for 20 hours and then diluted with 350 cm3 of water and subjected to extraction with 100 cm3 of ethyl acetate. The organic phase is washed with 100 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). 7.0 g of (3aS,4S,6R,7aR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol are obtained in the form of a thick white foam.

후처리

  1. extractionsubjected to extraction with 100 cm3 of ethyl acetate
  2. washThe organic phase is washed with 100 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-ceca9afd328b47debff17cb7110ae762
출처 데이터셋
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05739351

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