Water → tert-butyl (6R,7R)-6-[2-amino-2-(hydroxyimino)ethyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022707노트

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HRID 1022707 반응식
C(=O)([O-])O.[Na+].Cl.[NH2:7][OH:8].[C:9]([CH2:11][C@H:12]1[C@H:18]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[O:17][CH2:16][CH2:15][N:14]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13]1)#[N:10].O>CS(C)=O>[NH2:10][C:9](=[N:7][OH:8])[CH2:11][C@H:12]1[C@H:18]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[O:17][CH2:16][CH2:15][N:14]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13]1

참가 물질

6

반응물 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 66975920tert-butyl (6R,7R)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

생성물 1

HCID 86663870tert-butyl (6R,7R)-6-[2-amino-2-(hydroxyimino)ethyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate수율 108.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

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온도
80 °C

실험 절차

Sodium hydrogen carbonate (872 mg, 10.38 mmol) was added to a suspension of hydroxylamine monohydrochloride (721 mg, 10.38 mmol) in DMSO (3 mL), and the mixture was stirred at 80° C. for 15 min. The precipitate was filtered off, and a solution of tert-butyl (6R,7R)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (500 mg, 1.30 mmol) in DMSO (4 mL) was added to the filtrate. The reaction mixture was stirred at 80° C. overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (588 mg). This compound was used for the next reaction without purification.

후처리

  1. filtrationThe precipitate was filtered off
  2. stirringThe reaction mixture was stirred at 80° C. overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d9b419520b7c4e3cb54555168c21952c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722662B2

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