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

HRID 1920195ノート

反応式

HRID 1920195 の反応式
[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]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 21874358HCID 21874358、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-b009954757a644cc895148254555ea44
出典データセット
uspto-grants-2012_05
特許番号
US08168794B2

反応ノート

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