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

HRID 1607126Notes

Reaction equation

HRID 1607126 reaction equation
[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]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 444972Fumaric AcidHCID 198529363-(2-Amino-1,1-dimethylethylamino)-1-(3-methylbenzimidazol-4-yloxy)-propan-2-olHCID 200955153-Chloro-2,2-dimethyl-3-oxopropyl nitrate

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ae3506e273154b26af140435f0456d58
Source dataset
uspto-grants-1989_09
Patent number
US04863949

Reaction notes

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