Malic Acid → HCID 86737896, compound

HRID 1278315Notes

Reaction equation

HRID 1278315 reaction equation
C([N:11]([CH:15]([C:19]1C=CC=C[CH:20]=1)[C:16](Cl)=O)[CH2:12][CH:13]=[CH2:14])(OCC1C=CC=CC=1)=O.C(N(CC)CC)C.[C:32]([OH:40])(=[O:39])[CH:33]([CH2:35][C:36]([OH:38])=[O:37])[OH:34].[H][H].[O:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1>[Pd].CCOCC>[CH2:12]([NH:11][C:15]1[CH:19]=[CH:20][C:45]([CH2:46][C:47]([O:39][C:32](=[O:40])[CH:33]([CH2:35][C:36]([OH:38])=[O:37])[OH:34])=[O:43])=[CH:44][CH:16]=1)[CH:13]=[CH2:14]

Participants

8

Reactant 5

HCID 525Malic AcidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 86737897HCID 86737897, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86737896HCID 86737896, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A warm solution of 4-[N-carbobenzyloxy-(allylamino]phenylacetyl 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, and the solution is evaporated. The residue is crystallized from acetic acid to yield O-[4-(allylamino)phenylacetyl]malic acid.

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-46618e4175354b70b7ae6a4803003f35
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

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