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

HRID 2049090

Reaction equation

HRID 2049090 reaction equation
C([N:11]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[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:44]([OH:52])(=[O:51])[CH:45]([CH2:47][C:48]([OH:50])=[O:49])[OH:46].[H][H]>O1CCCC1.CCOCC>[CH2:21]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:51][C:44](=[O:52])[CH:45]([CH2:47][C:48]([OH:50])=[O:49])[OH:46])=[O:17])=[CH:19][CH:20]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 20437379N-carbobenzyloxy-4-(hexadecylamino)benzoyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 86736912O-[4-(hexadecylamino)benzoyl]malic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a warm solution of N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride and 1.3 g. (1 eq) triethylamine in 100 ml. ether is treated with 2 g. (14.9 m moles) 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-de465cf53f2b442588218722b46bc506
Source dataset
uspto-grants-1980_04
Patent number
US04196208

Linked notes

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