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

HRID 903411
Notes
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Reaction equation

HRID 903411 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3283
Diethyl Ether
Solvent
HCID 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 over 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-dcedddcd33fe4842aae174fff870ce11
Source dataset
uspto-grants-1980_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04227014

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes