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

HRID 1099485Notes

Reaction equation

HRID 1099485 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-09386b6eb54d4e93be235da811d7a293
Source dataset
uspto-grants-2012_03
Patent number
US08143437B2

Reaction notes

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