Triethylamine → (E)-tert-butyl 4-(4-methoxy-4-oxobut-2-enoyl)piperazine-1-carboxylate

HRID 869785

반응식

HRID 869785 반응식
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O-:6])=O.C(Cl)(=O)C(Cl)=O.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH3:9][O:8][C:1](=[O:7])/[CH:2]=[CH:3]/[C:4]([N:26]1[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]1)=[O:6]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21721168(E)-4-methoxy-4-oxobut-2-enoate

생성물 1

HCID 67312317(E)-tert-butyl 4-(4-methoxy-4-oxobut-2-enoyl)piperazine-1-carboxylate수율 21%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

Mono methyl fumarate (650 mg, 5.0 mmol) was taken up in 10 mL of CH2Cl2 and oxalyl chloride (420 μL, 5.0 mmol) was added. After a few drops of DMF was added, the reaction mixture was stirred at room temperature until all gas evolution had ceased (1 h). This freshly prepared solution of acid chloride was then added dropwise at 0° C. to a solution containing Boc-piperazine (930 mg) and triethylamine (1.0 mL, 7.5 mmol) in 20 mL of CH2Cl2. The resulting reaction mixture was stirred at room temperature for 1 h and washed with brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (CH2Cl2) afforded 310 mg of (E)-tert-butyl 4-(4-methoxy-4-oxobut-2-enoyl)piperazine-1-carboxylate (21% yield).

후처리

  1. custom(1 h)
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature for 1 h
  4. washwashed with brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatography (CH2Cl2)

출처 및 근거

ORD 기록
ord-600d3d67568f492d99d760ca17391ec9
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969354B2

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