Triethylamine → Benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate

HRID 1920195노트

반응식

HRID 1920195 반응식
[CH:1]12[NH:7][CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2]2.[P:18](Cl)(=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21].C(N(CC)CC)C>C(Cl)Cl>[CH2:20]([O:19][P:18]([N:7]1[CH:1]2[CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2]2)([O:22][CH2:23][CH3:24])=[O:25])[CH3:21]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 21874358HCID 21874358, 화합물

생성물 1

HCID 59455678Benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of benzyl 3,7-diazabicyclo[4.1.0]heptane-3-carboxylate (1.0 equiv.) in DCM (0.26M) was added diethyl phosphorochloridate (1.3 equiv.) and triethyl amine (1.5 equiv.). The reaction was stirred for 24 h, then concentrated to dryness. Added water and ethyl acetate, the organics were extracted, dried with Na2SO4, and concentrated. The crude was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (50% to 100% ethyl acetate) to yield benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate as a clear oil in 21% yield. LCMS (m/z): 369.0 (MH+).

후처리

  1. concentrationconcentrated to dryness
  2. extractionAdded water and ethyl acetate, the organics were extracted
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe crude was purified via silica gel column chromatography
  6. washeluting with ethyl acetate and hexanes (50% to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-b009954757a644cc895148254555ea44
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168794B2

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