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Tetrahydrofuran → 3-[1,1-Dimethyl-2-(2,2-dimethyl-3-nitroxypropanoylamino)-ethylamino]-1-(3-methylbenzimidazol-4-yloxy)-propan-2-ol fumarate

HRID 1607126
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HRID 1607126 반응식
[CH3:1][C:2]([CH3:11])([CH2:6][O:7][N+:8]([O-:10])=[O:9])[C:3](Cl)=[O:4].O1CCCC1.[NH2:17][CH2:18][C:19]([NH:22][CH2:23][CH:24]([OH:37])[CH2:25][O:26][C:27]1[C:35]2[N:34]([CH3:36])[CH:33]=[N:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)([CH3:21])[CH3:20].[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42]>CC(C)=O.C(Cl)Cl>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42].[CH3:21][C:19]([NH:22][CH2:23][CH:24]([OH:37])[CH2:25][O:26][C:27]1[C:35]2[N:34]([CH3:36])[CH:33]=[N:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)([CH3:20])[CH2:18][NH:17][C:3](=[O:4])[C:2]([CH3:11])([CH3:1])[CH2:6][O:7][N+:8]([O-:10])=[O:9]
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참가 물질

7

반응물 4

HCID 8028Tetrahydrofuran2회HCID 444972Fumaric AcidHCID 198529363-(2-Amino-1,1-dimethylethylamino)-1-(3-methylbenzimidazol-4-yloxy)-propan-2-olHCID 200955153-Chloro-2,2-dimethyl-3-oxopropyl nitrate

생성물 1

HCID 137153783-[1,1-Dimethyl-2-(2,2-dimethyl-3-nitroxypropanoylamino)-ethylamino]-1-(3-methylbenzimidazol-4-yloxy)-propan-2-ol fumarate

시약·촉매·용매 2

HCID 180Acetone용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1.4 g. 2,2-dimethyl-3-nitroxypropanoyl chloride in 50 ml. dry tetrahydrofuran is added dropwise at ambient temperature to a solution of 2.3 g. 3-(2-amino-1,1-dimethylethylamino)-1-(3-methylbenzimidazol-4-yloxy)-propan-2-ol in 150 ml. dry tetrahydrofuran, followed by further stirring for 2 hours. The reaction mixture is evaporated and chromatographed on silica gel with methylene chloride/methanol (4:2 v/v). The product obtained (2.0 g.) is dissolved in 60 ml. methylene chloride and mixed with 0.54 g. fumaric acid in 100 ml. acetone. The precipitate which separates out after the addition of 200 ml. diethyl ether is filtered off with suction and dried. There are obtained 2.3 g. (53% of theory) of the desired product in the form of crystals; m.p. 187°-190° C.

후처리

  1. customThe reaction mixture is evaporated
  2. customchromatographed on silica gel with methylene chloride/methanol (4:2 v/v)
  3. customThe product obtained (2.0 g.)
  4. dissolutionis dissolved in 60 ml
  5. additionafter the addition of 200 ml
  6. filtrationdiethyl ether is filtered off with suction
  7. customdried
  8. customThere are obtained 2.3 g

출처 및 근거

ORD 기록
ord-ae3506e273154b26af140435f0456d58
출처 데이터셋
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04863949

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