Malic Acid → HCID 86737657, compound

HRID 128339Notes

Reaction equation

HRID 128339 reaction equation
C([N:11]([CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19](Cl)=[O:20])=[CH:14][CH:13]=1)(OCC1C=CC=CC=1)=O.C(N(CC)CC)C.[C:37]([OH:45])(=[O:44])[CH:38]([CH2:40][C:41]([OH:43])=[O:42])[OH:39].[H][H]>O1CCCC1.[Pd].CCOCC>[CH:24]1([CH2:23][CH2:22][NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:44][C:37](=[O:45])[CH:38]([CH2:40][C:41]([OH:43])=[O:42])[OH:39])=[O:20])=[CH:14][CH:13]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

8

Reactant 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 23469307HCID 23469307, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86737657HCID 86737657, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A warm solution of 4-[N-carbobenzyloxy-(2-cyclohexylethylamino)]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-(2-cyclohexylethylamino)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-46c066f6556d4990ac0d5c42c617f44a
Source dataset
uspto-grants-1981_03
Patent number
US04259352

Reaction notes

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