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

HRID 227346노트

반응식

HRID 227346 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 116115921-[{(alpha-Benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid수율 49%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2158f0c19300418b98a285afee529285
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560483B2

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