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Dimethylformamide → 3(S*)-Azido-6(R*)-phenylperhydroazepin-2-one

HRID 569754
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HRID 569754 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].CN(C)C=O.Br[CH:11]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][NH:13][C:12]1=[O:24]>C(OCC)(=O)C>[N:1]([C@@H:11]1[CH2:17][CH2:16][C@@H:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:14][NH:13][C:12]1=[O:24])=[N+:2]=[N-:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 140034303-Bromo-6-phenylperhydroazepin-2-one

생성물 1

HCID 140034353(S*)-Azido-6(R*)-phenylperhydroazepin-2-one

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

2.0 g of sodium azide were added to 20 ml of dimethylformamide containing 1.6 g of 3-bromo-6-phenylperhydroazepin-2-one (Isomer A) [prepared as described in step (e) above]. The mixture was stirred for 6 hours at 60° C. and then diluted with ethyl acetate, washed with water three times and dried over anhydrous magnesium sulfate. The solvent was then distilled off. The crystalline residue was triturated in a 1:1 by volume mixture of methylene chloride and diisopropyl ether and then collected by filtration, to give 1.14 g of the title compound melting at 150°-152° C. (with decomposition).

후처리

  1. custom[prepared as described in step (e) above]
  2. washwashed with water three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. customThe crystalline residue was triturated in a 1:1 by volume mixture of methylene chloride and diisopropyl ether
  6. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-16ad80cb1eef4f9c8a7b6958ec7980db
출처 데이터셋
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04734410

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