Hydroxyamine hydrochloride → 3-[tert-butyl(diphenyl)silyl]oxy-N'-hydroxypropanimidamide

HRID 385961노트

반응식

HRID 385961 반응식
[Si:1]([O:18][CH2:19][CH2:20][C:21]#[N:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:24][OH:25].C(=O)(O)[O-].[Na+]>CO>[Si:1]([O:18][CH2:19][CH2:20]/[C:21](=[N:24]/[OH:25])/[NH2:22])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 108287163-(Tert-butyldiphenylsilyloxy)propanenitrile

생성물 1

HCID 108548133-[tert-butyl(diphenyl)silyl]oxy-N'-hydroxypropanimidamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 3-{[tert-butyl(diphenyl)silyl]oxy}propanenitrile (4.4 g, 14.2 mmol) in methanol (40 ml) was added hydroxylamine hydrochloride (8.9 g, 128 mmol) and sodium bicarbonate (11.9 g, 142 mmol). The mixture was heated at reflux for 48 hours. The mixture was then cooled to room temperature, the solvent was evaporated, ice water was added, and the resulting solution was extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (50-100% ethyl acetate in hexanes) to afford the title compound.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 hours
  3. customthe solvent was evaporated
  4. additionice water was added
  5. extractionthe resulting solution was extracted with ethyl acetate (2×)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified via silica gel chromatography (50-100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-77cdbc2d4af54a2d857c8ebed1a6ced4
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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