Hydrochloric Acid → Diethyl(2-((tert-butoxycarbonyl)amino)ethyl)(cyclopropyl)malonate

HRID 714920

반응식

HRID 714920 반응식
[CH:1]1([CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].O1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])S1(=O)=O.Cl>CN(C)C=O>[CH2:13]([O:12][C:10](=[O:11])[C:4]([CH2:21][CH2:20][NH:19][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH:1]1[CH2:3][CH2:2]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:14]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 127044081,3-Diethyl 2-cyclopropylpropanedioateHCID 235840203-Boc-1,2,3-oxathiazolidine 2,2-dioxide

생성물 1

HCID 117974976Diethyl(2-((tert-butoxycarbonyl)amino)ethyl)(cyclopropyl)malonate수율 50.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of diethyl cyclopropylmalonate (7.7 g) obtained in Step A of Example 388 in N,N-dimethylformamide (90 mL) was added sodium hydride (60% in mineral oil, 1.8 g), and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added tert-butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (9.4 g) at the same temperature, and the mixture was stirred at 0° C. for 2 hr. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (6.7 g).

후처리

  1. stirringthe mixture was stirred at 0° C. for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-5794d271586e43f4bd5ee8e6613b8f76
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187453B2

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