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

HRID 2166998노트

반응식

HRID 2166998 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d632c73ed8c04d9480f4f695ecf513c4
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09044389B2

반응 노트

불러오는 중…