Malic Acid → HCID 86737429, compound

HRID 1389096Notes

Reaction equation

HRID 1389096 reaction equation
C([N:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][C:13]=1[F:21])(OCC1C=CC=CC=1)=O.C(N(CC)CC)C.[C:45]([OH:53])(=[O:52])[CH:46]([CH2:48][C:49]([OH:51])=[O:50])[OH:47].[H][H]>O1CCCC1.CCOCC>[F:21][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:12]=1[NH:11][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:16]([O:52][C:45](=[O:53])[CH:46]([CH2:48][C:49]([OH:51])=[O:50])[OH:47])=[O:17]

Participants

7

Reactant 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 20536451HCID 20536451, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86737429HCID 86737429, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A warm solution of N-carbobenzyloxy-3-fluoro-4-(hexadecylamino)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 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% Pd(C) 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-fluoro-4-(hexadecylamino)benzoyl]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-cb606b7df47944f8a5c1a9b8e7b8e8c0
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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