Malic Acid → HCID 86737303, compound

HRID 904494Notes

Reaction equation

HRID 904494 reaction equation
C([N:11]([CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]=[CH2:35])[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:43]([OH:51])(=[O:50])[CH:44]([CH2:46][C:47]([OH:49])=[O:48])[OH:45].[H][H]>O1CCCC1.[Pd].CCOCC>[CH2:21]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:50][C:43](=[O:51])[CH:44]([CH2:46][C:47]([OH:49])=[O:48])[OH:45])=[O:17])=[CH:19][CH:20]=1)[CH2:22][CH2:23][CH:24]=[CH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]=[CH2:35]

Participants

8

Reactant 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 54048902HCID 54048902, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86737303HCID 86737303, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a warm solution of N-carbobenzyloxy-4-(4,14-pentadecadienylamino)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 wahsed 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 white crystals.

Workup

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

Sources & evidence

ORD record
ord-d91652d05d774f8589b8d58ae0ae05d6
Source dataset
uspto-grants-1980_10
Patent number
US04230878

Reaction notes

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