Citric Acid → 1-[{(alpha-Benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid

HRID 457277ノート

反応式

HRID 457277 の反応式
C([CH:9]([O:16][C:17]([NH:19][CH2:20][C:21]1([CH2:27][C:28]([OH:30])=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.[CH:31]1[CH:36]=[C:35](Cl)[CH:34]=[C:33]([C:38]([O:40]O)=[O:39])[CH:32]=1.C([O-])(O)=O.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:38]([O:40][CH:9]([O:16][C:17]([NH:19][CH2:20][C:21]1([CH2:27][C:28]([OH:30])=[O:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:39])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:31][CH:32]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 116544391-{[(alpha-Benzoylbenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid

生成物 1

HCID 116115921-[{(alpha-Benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid収率 49.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-{[(α-benzoylbenzyloxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid (61) (1.89 g, 4.6 mmol) in 40 mL of CH2Cl2 was added 77% mCPBA (2.07 g, 9.2 mmol) and NaHCO3 (0.78 g, 9.2 mmol), respectively, at room temperature and the resulting mixture was stirred at room temperature overnight. The reaction mixture was acidified with 10% citric acid and extracted with CH2Cl2. The organic extract was washed with brine and dried over Na2SO4. After removing the solvent under reduced pressure, the residue was purified by reverse phase preparative HPLC (acetonitrile-water, 0.1% formic acid) to afford 960 mg (49%) of the title compound (59). 1H NMR (CDCl3, 400 MHz): δ 1.58–1.35 (m, 10H), 2.34 (s, 2H), 3.26 (dd, J=6.8, 0.8 Hz, 2H), 5.38 (t, J=6.8 Hz, 1H), 7.46–7.26 (m, 5H), 7.63–7.55 (m, 3H), 7.89 (s, 1H), 8.08 (dd, J=8.8, 1.2 Hz, 2H).

後処理

  1. extractionextracted with CH2Cl2
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent under reduced pressure
  6. customthe residue was purified by reverse phase preparative HPLC (acetonitrile-water, 0.1% formic acid)

出典と根拠

ORDレコード
ord-c7c5e6cea7f549fab939597a00516974
出典データセット
uspto-grants-2007_03
特許番号
US07186855B2

反応ノート

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