Lactic Acid → HCID 20536462, compound

HRID 1389095Notes

Reaction equation

HRID 1389095 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:28]([OH:33])(=[O:32])[CH:29]([CH3:31])O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH:29]([C:28]([OH:33])=[O:32])[CH3:31])=[O:5]

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 69252-Methylbenzenesulfonic acidHCID 205364112-Fluoro-4-(hexadecylamino)benzoic acid

Product 1

HCID 20536462HCID 20536462, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask containing 10.0 g 2-fluoro-4-(hexadecylamino)-benzoic acid, 3.3 g. lactic acid, 500 mg. toluenesulfonic acid and 500 ml. toluene is equipped with a Soxhlet extractor charged with activated 4 A Linde molecular sieves. The solution is refluxed for 24 hours, during which time the Soxhlet extractor is charged twice more with fresh sieves. The hot solution is filtered and left to cool, whereupon 1-carboxyethyl 2-fluoro-4-(hexadecylamino)benzoate separates as off-white crystals.

Workup

  1. additioncharged
  2. temperatureThe solution is refluxed for 24 hours, during which time the Soxhlet extractor
  3. additionis charged twice more with fresh sieves
  4. filtrationThe hot solution is filtered
  5. waitleft
  6. temperatureto cool, whereupon 1-carboxyethyl 2-fluoro-4-(hexadecylamino)benzoate

Sources & evidence

ORD record
ord-21d3810c441940a5b666ea6f34bb2720
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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