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

HRID 584544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 584544
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1f2c6d1e53834bf4b387872a0b530558
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927036B2

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