HCID 14853142, compound → HCID 178513938, compound

HRID 1110965Notes

Reaction equation

HRID 1110965 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[C:7]([CH2:9][C:10]([F:16])([F:15])[C:11]([O:13]C)=O)[N:8]=1)([O-:3])=[O:2].[F:17][C:18]([F:24])([CH2:22][NH2:23])[C:19]([NH2:21])=[O:20]>CO>[N+:1]([C:4]1[NH:5][CH:6]=[C:7]([CH2:9][C:10]([F:16])([F:15])[C:11]([NH:23][CH2:22][C:18]([F:24])([F:17])[C:19]([NH2:21])=[O:20])=[O:13])[N:8]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14853142HCID 14853142, compoundHCID 178501025HCID 178501025, compound

Product 1

HCID 178513938HCID 178513938, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(2'-nitroimidazolyl)-2,2-difluoropropionate (10.0 g, 42.5 mmol) in methanol (60 ml), 2,2-difluoro-3-amino-propionic acid amide (10.4 g, 83.8 mmol) was added and reacted for 20 hours at a room temperature while stirring. Then, insoluble fraction was filtered off from the reaction mixture. The filtrate was concentrated, subjected to silica gel column chromatography and recrystallized from ethanol to obtain 3-[3'-(2"-nitroimidazolyl)-2',2'-difluoropropionylamino]-2,2-difluoropropionic acid amide (4.98 g). m.p. 134.5°-135.5° C.

Workup

  1. customreacted for 20 hours at a room temperature
  2. filtrationThen, insoluble fraction was filtered off from the reaction mixture
  3. concentrationThe filtrate was concentrated
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-49b7ca0a65f64474b0141d335af14174
Source dataset
uspto-grants-1990_12
Patent number
US04977273

Reaction notes

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