Malic Acid → O-[4-(16-bromohexadecylamino)benzoyl]malic acid

HRID 648317Notes

Reaction equation

HRID 648317 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][CH2:36][Br:37])[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:45]([OH:53])(=[O:52])[CH:46]([CH2:48][C:49]([OH:51])=[O:50])[OH:47].[H][H]>O1CCCC1.[Pd].CCOCC>[Br:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:52][C:45](=[O:53])[CH:46]([CH2:48][C:49]([OH:51])=[O:50])[OH:47])=[O:17])=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 20482544N-Carbobenzyloxy-4-(16-bromohexadecylamino)benzoyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 86737437O-[4-(16-bromohexadecylamino)benzoyl]malic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a warm solution of N-carbobenzyloxy-4-(16-bromohexadecylamino)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% palladium-on-carbon 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-09b95193f2cc4782849fe3f01ec2aa30
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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