Hydroxyamine hydrochloride → 5-(Hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

HRID 2166998Notes

Reaction equation

HRID 2166998 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[F:9][C:10]([F:24])([F:23])[CH2:11][NH:12][C:13]([C:15]1[S:16][C:17]([CH:21]=O)=[CH:18][C:19]=1[CH3:20])=[O:14]>C1COCC1.O.CS(C)=O>[F:9][C:10]([F:24])([F:23])[CH2:11][NH:12][C:13]([C:15]1[S:16][C:17]([CH:21]=[N:7][OH:8])=[CH:18][C:19]=1[CH3:20])=[O:14]

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866580355-Formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

Product 1

HCID 866580365-(Hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium acetate (90 mg) is added to a solution of hydroxylamine hydrochloride (60 mg) and 5-formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (190 mg) in THF (5 ml), water (1 ml) and DMSO (1 ml). After 3 hours at room temperature, the reaction is quenched with water. The reaction mixture is extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and concentrated in vacuo to yield 5-(hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide. The crude product obtained (206 mg, yellowish oil) is used without further purification. MS (HPLC/MS): 267 (MH+). Retention time: 2.56 min and 2.64 min (two diastereoisomers).

Workup

  1. customthe reaction is quenched with water
  2. extractionThe reaction mixture is extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d632c73ed8c04d9480f4f695ecf513c4
Source dataset
uspto-grants-2015_06
Patent number
US09044389B2

Reaction notes

Loading…