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

HRID 390764ノート

反応式

HRID 390764 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-815a7e235a2845ba9c6885b299334ea9
出典データセット
uspto-grants-2013_02
特許番号
US08383659B2

反応ノート

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