Malic Acid → O-[4-(8-cyclohexyloctylamino)benzoyl]malic acid

HRID 905272Notes

Reaction equation

HRID 905272 reaction equation
C([N:11]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1)(OCC1C=CC=CC=1)=O.C(N(CC)CC)C.[C:42]([OH:50])(=[O:49])[CH:43]([CH2:45][C:46]([OH:48])=[O:47])[OH:44].[H][H]>O1CCCC1.CCOCC>[CH:29]1([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([O:49][C:42](=[O:50])[CH:43]([CH2:45][C:46]([OH:48])=[O:47])[OH:44])=[O:17])=[CH:14][CH:13]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 20475782N-carbobenzyloxy-4-(8-cyclohexyloctylamino)benzoyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 86737260O-[4-(8-cyclohexyloctylamino)benzoyl]malic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a warm solution of N-carbobenzyloxy-4-(8-cyclohexyloctylamino)benzoyl chloride and 1.3 g. triethylamine in 100 ml. ether is treated with 2 g. malic acid. An immediate precipitate forms, but the mixture is refluxed for one hour and filtered while hot. The solid is washed several times with hot ether, then the ether is evaporated to yield a white solid. The product is dissolved in tetrahydrofuran (100 ml.) and hydrogenated ove 600 mg. 10% Pd(C) at 50 psi until hydrogen uptake stops. The catalyst is filtered, the solution is evaporated, and the residue is crystallized from acetic acid to yield the title compound as a tan, crystalline mass.

Workup

  1. temperatureAn immediate precipitate forms, but the mixture is refluxed for one hour
  2. filtrationfiltered while hot
  3. washThe solid is washed several times with hot ether
  4. customthe ether is evaporated
  5. customto yield a white solid
  6. filtrationThe catalyst is filtered
  7. customthe solution is evaporated
  8. customthe residue is crystallized from acetic acid

Sources & evidence

ORD record
ord-094b9cce251d4e3aa4456b71e18b119b
Source dataset
uspto-grants-1983_12
Patent number
US04423051

Reaction notes

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