Malic Acid → O-(4-hexadecylamino-2-thiophenecarbonyl)malic acid

HRID 850986Notes

Reaction equation

HRID 850986 reaction equation
C([N:11]([C:28]1[CH:29]=[C:30]([C:33](Cl)=[O:34])[S:31][CH:32]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(OCC1C=CC=CC=1)=O.C(N(CC)CC)C.[C:43]([OH:51])(=[O:50])[CH:44]([CH2:46][C:47]([OH:49])=[O:48])[OH:45].[H][H]>O1CCCC1.[Pd].CCOCC>[CH2:12]([NH:11][C:28]1[CH:29]=[C:30]([C:33]([O:50][C:43](=[O:51])[CH:44]([CH2:46][C:47]([OH:49])=[O:48])[OH:45])=[O:34])[S:31][CH:32]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 205036214-[N-(carbobenzyloxy)-N-hexadecylamino]-2-thiophenecarbonyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 86738856O-(4-hexadecylamino-2-thiophenecarbonyl)malic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A warm solution of 4-[N-(carbobenzyloxy)-N-(hexadecyl)amino]-2-thiophenecarbonyl chloride and 1.3 g. of 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, and the solution is evaporated. The residue is crystallized from acetic acid to yield the product as a white solid.

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. customthen the 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-dd278f15741c4545b496cd60e1156566
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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