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

HRID 2061420ノート

反応式

HRID 2061420 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f058170d53ee493a8dcac81faf1f1344
出典データセット
uspto-grants-2012_10
特許番号
US08283310B2

反応ノート

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