1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[{(alpha-Benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid

HRID 584543ノート

反応式

HRID 584543 の反応式
C1CCN2C(=NCCC2)CC1.[C:12]([O:20][CH:21]([O:28][C:29]([NH:31][CH2:32][C:33]1([CH2:39][C:40]([O:42]CCC#N)=[O:41])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[C:12]([O:20][CH:21]([O:28][C:29]([NH:31][CH2:32][C:33]1([CH2:39][C:40]([OH:42])=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

4

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2 回HCID 668107932-Cyanoethyl 1-{[(alpha-Benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

生成物 1

HCID 116115921-[{(alpha-Benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid収率 4.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

DBU (79.2 mg, 78 μL, 0.520 mmol) was added to a solution of 2-cyanoethyl 1-{[(α-benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-cyclohexane acetate (11) (166 mg, 0.347 mmol) in 10 mL of CH2Cl2 at −10° C. The reaction mixture was stirred at 0° C. for 1 hour, then allowed to warm to room temperature, stirred for two hours and cooled to 0° C. Another 78 μL of DBU was added, the reaction mixture was stirred for 3 hours at 0° C. and then allowed to warm to room temperature. The reaction mixture was diluted with CH2Cl2, washed with citric acid and brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by reversed phase HPLC to afford 7 mg (4.7%) of the title compound. M.p. 75.5-76.0° C. 1H NMR (CDCl3): δ 8.08 (2H, dd, J=8.8, 1.2 Hz); 7.89 (1H, s); 7.63-7.55 (3H, m); 7.46-7.26 (5H, m); 5.38 (1H, t, J=6.8 Hz); 3.26 (2H, dd, J=6.8, 0.8 Hz); 2.34 (2H, s); 1.58-1.35 (10 H, m). MS (ESI) m/z 424 (M−H−).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for two hours
  3. temperaturecooled to 0° C
  4. stirringthe reaction mixture was stirred for 3 hours at 0° C.
  5. temperatureto warm to room temperature
  6. washwashed with citric acid and brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by reversed phase HPLC

出典と根拠

ORDレコード
ord-9a2cb91573e24f2c9af2e47c091e7d39
出典データセット
uspto-grants-2005_08
特許番号
US06927036B2

反応ノート

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