Malic Acid → HCID 86739349, compound

HRID 325563Notes

Reaction equation

HRID 325563 reaction equation
C([N:11]([CH:15]([C:19]1C=CC=[CH:21][CH:20]=1)C(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:44]=[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:21]=[CH:20][CH:19]=1)[CH:13]=[CH2:14]

Participants

8

Reactant 5

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

Product 1

HCID 86739349HCID 86739349, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A warm solution of 3-[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-[3-(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-76510484163f43bb8bcc9a804a281b82
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Reaction notes

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