Hydrochloric Acid → 1-(Hept-6-enyl)cyclopropane-1-sulfonamide

HRID 2061420노트

반응식

HRID 2061420 반응식
Cl.O1CCOCC1.[CH2:8]([C:15]1([S:18]([NH:21]C(=O)OC(C)(C)C)(=[O:20])=[O:19])[CH2:17][CH2:16]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14]>O>[CH2:8]([C:15]1([S:18]([NH2:21])(=[O:19])=[O:20])[CH2:17][CH2:16]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59366234Tert-butyl 1-(hept-6-enyl)cyclopropylsulfonylcarbamate

생성물 1

HCID 593662391-(Hept-6-enyl)cyclopropane-1-sulfonamide수율 92.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

4.0M HCl in dioxane (4.285 mL, 17.14 mmol) was added to tert-butyl 1-(hept-6-enyl)cyclopropylsulfonylcarbamate (544 mg, 1.714 mmol) and stirred at r.t. for 3 h. Poured into water, extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated in vacuo. The residue was purified by Biotage column, eluted with gradient 5%˜60% EtOAc-Hexane to afford the desired product 1-(hept-6-enyl)cyclopropane-1-sulfonamide (350 mg, 1.578 mmol, 92% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-D) ppm 0.82-0.94 (m, 2 H) 1.28-1.53 (m, 8 H) 1.84-1.97 (m, 2 H) 2.06 (q, J=6.94 Hz, 2 H) 4.49 (b, NH2) 4.89-5.07 (m, 2 H) 5.70-5.90 (m, 1 H).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Biotage column
  7. washeluted with gradient 5%˜60% EtOAc-Hexane

출처 및 근거

ORD 기록
ord-f058170d53ee493a8dcac81faf1f1344
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283310B2

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