Ethanolamine → HCID 178523466, compound

HRID 1110967Notes

Reaction equation

HRID 1110967 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[C:7]([CH2:9][C:10]([F:22])([F:21])[CH2:11][O:12][CH2:13][C:14]([F:20])([F:19])[C:15]([O:17]C)=O)[N:8]=1)([O-:3])=[O:2].[CH2:23]([CH2:25][NH2:26])[OH:24]>O1CCOCC1>[OH:24][CH2:23][CH2:25][NH:26][C:15](=[O:17])[C:14]([F:20])([F:19])[CH2:13][O:12][CH2:11][C:10]([F:22])([F:21])[CH2:9][C:7]1[N:8]=[C:4]([N+:1]([O-:3])=[O:2])[NH:5][CH:6]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 178501027HCID 178501027, compound

Product 1

HCID 178523466HCID 178523466, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 3-[3'-(2"-nitroimidazolyl)-2',2'-difluoropropoxy]-2,2-difluoropropionate (1.0 g, 3.0 mmol) in dioxane (10 ml), ethanolamine (370 mg, 6.0 mmol) was added and reacted for 5 hours at a room temperature with stirring. The reaction solution was concentrated and partitioned between ethyl acetate and water. The ethyl acetate phase was dried over magnesium sulfate, filtered, concentrated and purified by silica gel column chromatography to obtain 3-[3'-(2"-nitroimidazolyl)-2',2'-difluoropropoxy]-2,2-difluoropropionic acid hydroxyethylamide (550 mg). m.p. 67°-68° C. 1H-NMR (DMSO-d6): δ=3.24-3.76 (5H, m), 4.14 (2H, t, --CF2CH2 --, J=13 Hz), 4.22 (2H, t, --OCH2, J=14 Hz), 4.88 (1H, brt, --OH), 5.24 (2H, t, CH2CF2, J= 15 Hz), 7.42 (1H, d, H5 "), 7.98 (1H, d, H4 "), 8.93 (1H, brt, NH)

Workup

  1. customreacted for 5 hours at a room temperature
  2. concentrationThe reaction solution was concentrated
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-088bea4ed7074081b5d704e205787585
Source dataset
uspto-grants-1990_12
Patent number
US04977273

Reaction notes

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