Methanol → (1R,2S)-1-(((1,1-Dimethylethoxy)carbonyl)amino)-2-ethenylcyclopropanecarboxylic acid

HRID 522378

반응식

HRID 522378 반응식
[C:1]([O:5][C:6]([NH:8][C@:9]1([C:14]([O:16]CC)=[O:15])[CH2:11][C@H:10]1[CH:12]=[CH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].CO.C1COCC1>O>[C:1]([O:5][C:6]([NH:8][C@:9]1([C:14]([OH:16])=[O:15])[CH2:11][C@H:10]1[CH:12]=[CH2:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 10658673Ethyl (1R,2S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenylcyclopropanecarboxylate

생성물 1

HCID 10376443(1R,2S)-1-(((1,1-Dimethylethoxy)carbonyl)amino)-2-ethenylcyclopropanecarboxylic acid수율 98.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
45 °C

실험 절차

A round-bottom flask was charged with (1R,2S)-ethyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate (4 g, 15.67 mmol) and lithium hydroxide monohydrate (2.63 g, 62.7 mmol). Methanol (52.2 ml), THF (52.2 ml) and water (52.2 ml) were added. The mixture was heated (oil bath at 45° C.) overnight. The reaction mixture was concentrated to half-its volume in rotavap and the pH of the mixture was adjusted to pH=2-3 with aq 1M HCl. The mixture was extracted with dichloromethane (3×150 mL). The combined organic extracts were washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in rotavap to give the title compound (3.5 g, 15.40 mmol, 98% yield) as a white powder. No further purification was carried out.

후처리

  1. concentrationThe reaction mixture was concentrated to half-its volume in rotavap
  2. extractionThe mixture was extracted with dichloromethane (3×150 mL)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in rotavap

출처 및 근거

ORD 기록
ord-19565a8cd2074a4aaf9b61661348ae9e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328138B2

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