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

HRID 584544ノート

反応式

HRID 584544 の反応式
[CH:1]1[CH:6]=[C:5](Cl)[CH:4]=[C:3]([C:8]([O:10]O)=[O:9])[CH:2]=1.C([O-])(O)=O.[Na+].C([CH:25]([O:32][C:33]([NH:35][CH2:36][C:37]1([CH2:43][C:44]([OH:46])=[O:45])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=O)C1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:8]([O:10][CH:25]([O:32][C:33]([NH:35][CH2:36][C:37]1([CH2:43][C:44]([OH:46])=[O:45])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1)=[O:34])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:1][CH:2]=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%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

mCPBA (77%, 2.07 g, 9.24 mmol) and NaHCO3 (0.78 g, 9.24 mmol) was added to a solution of 1-{[(α-benzoylbenzyloxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid (15) (1.89 g, 4.62 mmol) in 40 mL of CH2Cl2 at room temperature and the resulting mixture was stirred at room temperature overnight. The reaction mixture was acidified with citric acid, extracted with CH2Cl2 and the organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC to afford 960 mg (49%) of the title compound.

後処理

  1. extractionextracted with CH2Cl2
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-1f2c6d1e53834bf4b387872a0b530558
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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